[ CAS No. 6974-32-9 ] {[proInfo.proName]}

Name: 6974-32-9|(2S,3R,4R,5R)-2-Acetoxy-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate|98%
Brand: Ambeed
SKU: A139103
Price: 5.0 USD
Availability: InStock
Rating: 92 (30 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 6974-32-9 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 6974-32-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 6974-32-9 ]

SDS Specification

Alternatived Products of [ 6974-32-9 ]

Product Details of [ 6974-32-9 ]

CAS No. :	6974-32-9	MDL No. :	MFCD00005357
Formula :	C₂₈H₂₄O₉	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GCZABPLTDYVJMP-CBUXHAPBSA-N
M.W :	504.48	Pubchem ID :	81455
Synonyms :

Calculated chemistry of [ 6974-32-9 ]

Physicochemical Properties

Num. heavy atoms :	37
Num. arom. heavy atoms :	18
Fraction Csp3 :	0.21
Num. rotatable bonds :	12
Num. H-bond acceptors :	9.0
Num. H-bond donors :	0.0
Molar Refractivity :	128.42
TPSA :	114.43 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.37 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.6
Log Po/w (XLOGP3) :	5.65
Log Po/w (WLOGP) :	3.58
Log Po/w (MLOGP) :	3.34
Log Po/w (SILICOS-IT) :	3.42
Consensus Log Po/w :	3.92

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	1.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-6.1
Solubility :	0.000405 mg/ml ; 0.000000803 mol/l
Class :	Poorly soluble
Log S (Ali) :	-7.82
Solubility :	0.00000768 mg/ml ; 0.0000000152 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-6.72
Solubility :	0.0000952 mg/ml ; 0.000000189 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	4.78

Safety of [ 6974-32-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 6974-32-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 6974-32-9 ]
Downstream synthetic route of [ 6974-32-9 ]

[ 6974-32-9 ] Synthesis Path-Upstream 1~12

1
[ 6974-32-9 ]
[ 2140-61-6 ]

Reference： [1] Tetrahedron Letters, 2001, vol. 42, # 6, p. 1061 - 1063
[2] Chemical and Pharmaceutical Bulletin, 1988, vol. 36, # 7, p. 2673 - 2678

2
[ 6974-32-9 ]
[ 22224-41-5 ]

Yield	Reaction Conditions	Operation in experiment
65.1%	With hydrogenchloride In dichloromethane for 2.5 h; Cooling with ice	The synthesis of compound vi: The compound v (2.57mmol) was dissolved in 26 ml dry dichloromethane and dry HCl gas was slowly introduced into an ice-water bath for 2.5 hours. The solution was washed with 19.5ml ice water and the organic layer was separated. The organic layer was washed with saturated sodium bicarbonate until the water layer shows weak alkaline, and then washed with ice water until the water layer shows neutral, dried over anhydrous sodium sulfate for more than 4 hours, and then drawn off under a reduced pressure to obtain light yellow syrup. The syrup was recrystallized using the mixed solvent of hexane and dichloromethane, so as to obtain the white solid compound vi (65.1percent). ¹H NMR(CDCl₃) δppm: 7.36.similar.8.14 (m, 15H, OBz), 6.68 (d, J=4.4Hz, 1H, H-1), 5.59 (dd, 1H, H-3), 4.64.similar.4.80 (m, 4H, H-2, H-4 and H-5). M,p, 139.similar.140°C.

Reference： [1] Patent: EP2177527, 2010, A1, . Location in patent: Page/Page column 11
[2] Journal of Organic Chemistry, 1985, vol. 50, # 14, p. 2597 - 2598

3
[ 6974-32-9 ]
[ 115459-50-2 ]
[ 22224-41-5 ]

Reference： [1] Journal of Organic Chemistry, 1988, vol. 53, p. 85 - 88

4
[ 6974-32-9 ]
[ 52523-35-0 ]
[ 320-67-2 ]

Yield	Reaction Conditions	Operation in experiment
71%	Stage #1: at 55℃; for 12.5 h; Industry scale Stage #2: With methanol; sodium methylate In dimethyl sulfoxide; acetonitrile at 22 - 23℃; for 3.75 h;	Example 2 Coupling of Silyl 5-Azacytosine to Sugar and Deprotection A mixture of 2-[(trimethylsilyl)amino]-4-[(trimethylsilyl)oxy]-s-triazine (4.5 Kg), 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (8.8 Kg), anhydrous MeCN (34.6 Kg) and TfOH (600 g) were heated at 55° C. for 12.5 hours. The reaction mixture was cooled to 45° C., DMSO (29 Kg) was added, and the MeCN was evaporated at an internal temperature of <50° C. under vacuum until about 54 L of the solution. The solution was cooled to 23° C. MeOH (13.9 Kg) was added followed by a solution of 30percent NaOMe in MeOH solution (2.5 Kg) that was pre-diluted with MeOH (7.0 Kg). The solution was stirred at 23° C. for 35 minutes. When the reaction was complete MeOH (90.4 Kg) was added and the resulting slurry was stirred at 22° C. for 3 hours and 10 minutes and was then filtered and washed three times with MeOH (7.0 Kg each). The cake was dried under vacuum at below 70° C. for 9 hours and 20 minutes to give 3.2 Kg of 98.89percent purity crude azacitidine (71percent yield based on 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose).

Reference： [1] Patent: US2010/36112, 2010, A1, . Location in patent: Page/Page column 7

5
[ 6974-32-9 ]
[ 555-30-6 ]
[ 79439-78-4 ]
[ 6988-74-5 ]
[ 14215-97-5 ]

Reference： [1] European Journal of Medicinal Chemistry, 1981, vol. 16, # 3, p. 219 - 227

6
[ 6974-32-9 ]
[ 79439-66-0 ]
[ 79439-72-8 ]
[ 79439-70-6 ]
[ 6988-74-5 ]
[ 14215-97-5 ]

Reference： [1] European Journal of Medicinal Chemistry, 1981, vol. 16, # 3, p. 219 - 227
[2] European Journal of Medicinal Chemistry, 1981, vol. 16, # 3, p. 219 - 227
[3] European Journal of Medicinal Chemistry, 1981, vol. 16, # 3, p. 219 - 227

7
[ 6974-32-9 ]
[ 75-36-5 ]
[ 79439-79-5 ]
[ 6988-74-5 ]
[ 115459-50-2 ]
[ 14215-97-5 ]

Reference： [1] European Journal of Medicinal Chemistry, 1981, vol. 16, # 3, p. 219 - 227

8
[ 6974-32-9 ]
[ 39740-33-5 ]
[ 79439-71-7 ]
[ 79439-73-9 ]
[ 6988-74-5 ]
[ 14215-97-5 ]

Reference： [1] European Journal of Medicinal Chemistry, 1981, vol. 16, # 3, p. 219 - 227

9
[ 6974-32-9 ]
[ 3690-10-6 ]

Reference： [1] Tetrahedron Letters, 1994, vol. 35, # 10, p. 1597 - 1600

10
[ 6974-32-9 ]
[ 1094-61-7 ]

Reference： [1] Synthesis, 1981, # 5, p. 388 - 389
[2] Journal of the Chemical Society, 1957, p. 3727,3731

11
[ 6974-32-9 ]
[ 123318-82-1 ]

Reference： [1] Patent: US2012/10397, 2012, A1,
[2] Patent: US2012/10397, 2012, A1,
[3] Patent: EP2404926, 2012, A1,

12
[ 6974-32-9 ]
[ 163042-96-4 ]

Reference： [1] Patent: KR2015/10195, 2015, A,

[ 6974-32-9 ] Synthesis Path-Downstream 1~88

1
[ 6974-32-9 ]
[ 5991-01-5 ]

Yield	Reaction Conditions	Operation in experiment
	titanium tetrachloride; In dichloromethane;	Example 8 Preparation of 2,3,5-Tri-O-Benzoyl-alpha,beta-D-Ribofuranosyl Chloride To a solution of 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (3.02 g, 5.98 mmol) in dry dichloromethane (100 ml) was added via cannula a dichloromethane solution of titanium tetrachloride (1.13 g, 5.98 mmol, 5.98 ml of a 1M solution). The solution was stirred at room temperature for 1. 5 hours under argon, then washed with water (3*100 ml), dried over anhydrous magnesium sulfate and evaporated in vacuo to give the title compounds as a colourless oil (2.9 g, 1 00%). 1H nmr indicated it to be an approximately 1:1 mixture of alpha:beta-anomers. 1H nmr (CDCl3) delta ppm; 8.06-7.81 (m, 6H), 7.55-7.09 (m, 12H), 6.57 (d, 0.5H, J= 4.5 Hz, H-1 of alpha-anomer), 6.20 (s, 0.5H, H-1 of beta-anomer), 6.07 (dd, 0.5H,,J 4.6 Hz), 5.91 (d, 0.5H, J=4.5 Hz), 5.78 (dd, 0.5H, J= 7.0, 2.9 Hz), 5.48 (dd, 0.5H, J=7.0, 4.6 Hz), 4.96-4.85 (m, 2H), 4.64-4.55 (m, 1H).
	With titanium tetrachloride; In dichloromethane; at 23℃; for 2h;Inert atmosphere;	beta-1-O-Acetyl-2,3,5-O-benzoylribofuranose (11) (9, 5.91 g, 11.71 mmol) in CH2Cl2 (70mL) was added a solution of TiCl4 in CH2Cl2 (13mL, 1.0M).[12] The reaction was stirred at 23C for 2 hours, followed by quenching with deionized H2O (75 mL). The organic layer was separated, washed with deionized H2O (1 × 75 mL), dried over anhydrous MgSO4, and concentrated in vacuo. The crude material 1-chloro-2,3,5-tri-O-benzyl-alpha-D-arabinofuranose (11) was dissolved in CH3CN (20 mL) and used without further purification in the subsequent coupling step.
	With hydrogenchloride; In dichloromethane; at 0 - 8℃; for 6.5h;	Hydrogen chloride was bubbled into an ice-cold solution of 1 (0.80g, 1.58mmol) in methylene chloride (15mL) for 1.5h. After being kept at 2-8C for 5h, the solution was concentrated under vacuum. To the obtained crude 1-chloro derivative 3 was added a mixture of CH2Cl2 (7mL), MeOH (7mL) and H2O (1.5mL). The mixture was stirred for 1h at ambient temperature and diluted with CHCl3 (150mL). The organic phase was washed with 5% NaHCO3 (50mL), dried over Na2SO4 and evaporated to dryness. The obtained residue was applied to a chromatographic column (silica gel, 80cm3) and eluted with a linear ethyl acetate gradient (20?30%, v/v, 400mL). The fractions containing the product were collected and evaporated to yield 0.61g of colorless oil. To this ice-cooled residue in a mixture of anhydrous pyridine (0.3mL) and CH2Cl2 (10mL) was added benzoyl chloride (0.3mL, 2.58mmol), the reaction mixture was stirred for 20h at room temperature. After standard workup the obtained residue was applied to a chromatographic column (silica gel, 100cm3) and eluted with CHCl3/hexane (5:1, v/v, 500mL). The fractions containing the products 5 and 6 were collected and evaporation to dryness under vacuum. 5: Yield 50%;

Reference： [1]Journal of the Chemical Society,1957,p. 3727,3731
[2]Carbohydrate Research,1997,vol. 304,p. 257 - 260
[3]Patent: US2001/19823,2001,A1
[4]Nucleosides, nucleotides and nucleic acids,2013,vol. 32,p. 294 - 305
[5]Tetrahedron,2016,vol. 72,p. 6518 - 6527
[6]Organic Letters,2017,vol. 19,p. 6360 - 6363

2
[ 6974-32-9 ]
[ 7408-41-5 ]

Reference： [1]Carbohydrate Research,1992,vol. 232,p. 359 - 365
[2]Collection of Czechoslovak Chemical Communications,2012,vol. 77,p. 345 - 349
[3]Liebigs Annalen der Chemie,1980,vol. No.9,p. 1455 - 1469
[4]Organic and Biomolecular Chemistry,2012,vol. 10,p. 9601 - 9619
[5]Journal of Fluorine Chemistry,2008,vol. 129,p. 788 - 798
[6]European Journal of Medicinal Chemistry,2018,vol. 150,p. 268 - 281
[7]Synthetic Communications,2019,vol. 49,p. 3140 - 3147
[8]Tetrahedron Letters,1989,vol. 30,p. 1599 - 1600
[9]Journal of Heterocyclic Chemistry,2017,vol. 54,p. 436 - 449
[10]Journal of the Chemical Society,1965,p. 6864 - 6870
[11]Nucleosides, nucleotides and nucleic acids,2009,vol. 28,p. 238 - 259

3
[ 6974-32-9 ]
[ 760-32-7 ]
[ 201230-82-2 ]
[ 115141-23-6 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 3387 - 3389
[2]Tetrahedron,1992,vol. 48,p. 2013 - 2024
[3]Tetrahedron,2003,vol. 59,p. 2423 - 2434
[4]Bulletin of the Korean Chemical Society,2011,vol. 32,p. 1620 - 1624

4
[ 6974-32-9 ]
[ 10075-63-5 ]
[ 133009-61-7 ]
[ 133009-68-4 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 3731 - 3734

5
[ 6974-32-9 ]
[ 555-30-6 ]
[ 79439-78-4 ]
[ 6988-74-5 ]
[ 14215-97-5 ]

Reference： [1]European Journal of Medicinal Chemistry,1981,vol. 16,p. 219 - 227

6
[ 6974-32-9 ]
[ 136944-79-1 ]
[ 138786-93-3 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 159 - 166
[2]Journal of Medicinal Chemistry,1992,vol. 35,p. 917 - 924

7
[ 6974-32-9 ]
[ 81190-89-8 ]
[ 138786-91-1 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 917 - 924

8
[ 6974-32-9 ]
[ 138786-86-4 ]
[ 138786-90-0 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 917 - 924

9
[ 6974-32-9 ]
[ 18740-38-0 ]
[ 75860-83-2 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 1853 - 1858

10
[ 6974-32-9 ]
[ 930-33-6 ]
[ 999-97-3 ]
[ 80049-46-3 ]
[ 80049-42-9 ]
[ 80049-44-1 ]

Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 474 - 482
[2]Journal of Organic Chemistry,1982,vol. 47,p. 474 - 482
[3]Journal of Organic Chemistry,1982,vol. 47,p. 474 - 482

11
[ 6974-32-9 ]
[ 7397-68-4 ]
[ 105953-14-8 ]
[ 105953-15-9 ]

Reference： [1]Tetrahedron,1986,vol. 42,p. 1511 - 1528
[2]Tetrahedron,1986,vol. 42,p. 1511 - 1528

12
[ 6974-32-9 ]
[ 6623-81-0 ]
[ 37805-86-0 ]

Reference： [1]Chemische Berichte,1981,vol. 114,p. 1279 - 1286

13
[ 6974-32-9 ]
[ 7288-28-0 ]
[ 3180-76-5 ]

Yield	Reaction Conditions	Operation in experiment
163 mg	With poly(4,5-diphenyl-2-vinyloxazolium perchlorate); In acetonitrile; at 140℃; for 14h;Schlenk technique; Inert atmosphere;	A mixtureof thymine (0.33 mmol), BSA (85 muL, 0.35 mmol), and MeCN (3.0 mL) placed in a20-mL Schlenk tube with a cold finger was stirred under reflux (bath temp., 80 C) for 1h. After the mixture was cooled to rt, 1 (0.30 mmol) and 6 (15 mumol) were added andthe Young?s tap of the Schlenk tube was closed. The resulting mixture was stirred at140 C for 14 h. The reaction mass was cooled to 0 C and saturated NaHCO3solution (2 mL) was added to it, followed by EtOAc (2 mL). The organic phase wasseparated and the aqueous phase was back-extracted with EtOAc (4 x 4 mL). Thecombined organic layer was dried over Na2SO4 and evaporated to afford a crudematerial, which was purified by MPLC (size 60, MeOH:CH2Cl2 = 0:100 14:86). 3g(163 mg) was obtained in 95% yield. [alpha]D20 -85 (c 1.0, CHCl3) [lit.S6 [alpha]D22 -21.1 (c 1, CHCl3)]; 1H NMR (CDCl3) delta 1.59 (d, J = 1.1 Hz, 3H), 4.65 (dd, J = 12.3 and 3.5Hz, 1H), 4.68-4.72 (m, 1H), 4.89 (dd, J = 12.3 and 2.7 Hz, 1H), 5.75 (dd, J = 6.2 and6.2 Hz, 1H), 5.91 (dd, J = 6.2 and 3.8 Hz, 1H), 6.43 (d, J = 6.2 Hz, 1H), 7.16 (q, J = 1.1Hz, 1H), 7.31-7.44 (m, 4H), 7.46-7.65 (m, 5H), 7.91-8.02 (m, 4H), 8.12-8.16 (m, 2H),8.63 (br s, 1H); 13C NMR (CDCl3) delta 12.1, 63.9, 71.4, 73.3, 80.6, 86.8, 112.2, 128.3,128.5, 128.6, 128.9, 129.2, 129.6, 129.8, 129.9, 133.73, 133.78, 133.81, 134.8, 150.2,163.2, 165.3, 165.4, 166.0; HRMS (FAB) calcd for C31H26N2O9Na [M+Na]+ 593.1536,found 593.1546.

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 2155 - 2158
[2]Helvetica Chimica Acta,1995,vol. 78,p. 1705 - 1737
[3]Pharmaceutical Chemistry Journal,1989,vol. 23,p. 493 - 496
Khimiko-Farmatsevticheskii Zhurnal,1989,vol. 23,p. 699 - 702
[4]Nucleosides, nucleotides and nucleic acids,2005,vol. 24,p. 1249 - 1263
[5]European Journal of Medicinal Chemistry,1999,vol. 34,p. 809 - 824
[6]Tetrahedron Letters,2017,vol. 58,p. 1921 - 1924

14
[ 6974-32-9 ]
[ 115459-50-2 ]
[ 22224-41-5 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 85 - 88

15
[ 108-24-7 ]
[ 115459-50-2 ]
[ 6974-32-9 ]

Yield	Reaction Conditions	Operation in experiment
92.1%	With pyridine; at 40℃;Cooling with ice;	The synthesis of compound v: The compound iv (2.73mmol) was dissolved in 5ml dry pyridine, and the solution was slowly added dropwise with acetic anhydride (0.0276mol) in an ice water bath, then stirred for 30 minutes. Then, the ice water bath was removed, and the solution was stirred at a room temperature for 7 hours, and then heated up to 40C. This temperature was kept for an hour. The solution was added with 6.5g broken ice and then stirred until the broken ice was melted. The reaction solution was poured into 13 ml ice water and extracted with chloroform. The organic layer was washed sequentially with ice water, pre-cooled sulfuric acid (3mol/L) and saturated sodium bicarbonate until the water layer shows weak alkaline, then washed with ice water until the water layer shows neutral, dried over anhydrous sodium sulfate for more than 4 hours, and then drawn off under a reduced pressure, so as to obtain the light yellow syrup-like compound v (92.1%). 1H NMR(CDCl3) deltappm: 7.30?8.10 (m, 15H, OBz), 6.43 (s, 1H, H-1), 5.90 (m, 1H, H-3), 5.80 (d, 1H, H-2), 4.50?4.80 (m, 2H, H-5), 2.00 (s, 3H, CH3COO-).

Reference： [1]Patent: EP2177527,2010,A1 .Location in patent: Page/Page column 11
[2]Journal of Organic Chemistry,1985,vol. 50,p. 2597 - 2598
[3]Journal of Organic Chemistry,1988,vol. 53,p. 85 - 88

16
[ 6974-32-9 ]
[ 5539-46-8 ]
C₃₀H₂₅N₃O₈S [ No CAS ]

Reference： [1]Nucleosides and Nucleotides,1995,vol. 14,p. 313 - 316

17
[ 6974-32-9 ]
[ 18903-18-9 ]
5-((3R,4R,5R)-3,4-Bis-benzoyloxy-5-benzoyloxymethyl-tetrahydro-furan-2-ylamino)-thiazole-4-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Nucleosides and Nucleotides,1995,vol. 14,p. 313 - 316

18
[ 6974-32-9 ]
[ 77156-75-3 ]
1-((2R,3R,4R,5R)-3,4-Bis-benzoyloxy-5-benzoyloxymethyl-tetrahydro-furan-2-yl)-8-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Nucleosides and Nucleotides,1996,vol. 15,p. 889 - 898

19
[ 6974-32-9 ]
[ 405230-97-9 ]
[ 405231-08-5 ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2001,vol. 20,p. 1975 - 2000

20
[ 6974-32-9 ]
[ 3304-70-9 ]
[ 66657-09-8 ]

Reference： [1]Bioorganic and medicinal chemistry letters,2002,vol. 12,p. 3391 - 3394

21
[ 6974-32-9 ]
[ 69205-79-4 ]
2-amino-7-(2',3',5'-tri-O-benzoyl-D-ribofuranosyl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Tetrahedron,2004,vol. 60,p. 943 - 959

22
[ 6974-32-9 ]
[ 23956-12-9 ]
5-(2-hydroxyethyl)-2',3',5'-tri-O-benzoyl-uridine [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2004,vol. 2,p. 2103 - 2112

23
[ 6974-32-9 ]
[ 4928-88-5 ]
[ 39925-13-8 ]
[ 39925-12-7 ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2004,vol. 23,p. 715 - 724
[2]Journal of Organic Chemistry,2007,vol. 72,p. 173 - 179

24
[ 6974-32-9 ]
[ 15965-57-8 ]
2-chloro-4-methyl-1-[β-D-erythro-pentofuranosyl]-1H-benzimidazole [ No CAS ]

Reference： [1]Synlett,2005,p. 1301 - 1305

25
[ 6974-32-9 ]
[ 582313-57-3 ]
[ 750598-19-7 ]

Yield	Reaction Conditions	Operation in experiment
65%	With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 20 - 80℃; for 1.41667h;	N, O-BIS (TRIMETHYLSILYL) ACETAMIDE (BSA, 0.16 mL, 0.64 mmol) was added to a stirred suspension of 4-chloro-5-fluoro-7H-pyrrolo [2, 3-d] pyrimidine (0.1 g, 0. 58 mmol) in dry acetonitrile (4 mL). After stirring at room temperature for 10 min, 1-O-ACETYL-2, 3, 5,-TRI-0- BENZOYL-P-D-RIBOFURANOSE (0.322 g, 0.64 mmol) was added, followed by the addition of trimethylsily trifluoromethanesulfonate (0.115 mL, 0.64 mmol). The reaction was stirred at room temperature for 15 min after which it was transferred to a preheated oil bath at 80°C. After stirring for 1 hour at 80°C, the reaction was cooled to room temperature and diluted with EtOAc (25 mL). The organic phase was then sequentially washed with saturated. NAHCO3 and brine, dried (MGS04) and concentrated to provide the crude nucleoside. Purification by column chromatography (SI02, 10-25percent EtOAc in hexanes) provided protected nucleoside (6) as a white foam (232 mg, 65percent). 1H NMR (CDC13) B : 8.63 (s, 1H), 8. 11 (d, 2H, J= 7.1 Hz), 8.01 (d, 2H, J= 7.1 Hz), 7.91 (d, 2H, J= 7.1 Hz), 7. 65-7. 33 (M, 9H), 7.17 (d, 1H, J= 2.6 Hz), 6.69 (dd, 1H J= 6.2, 1.1 Hz), 6.09 (M, 2H), 4.87 (dd, 1H, J= 12. 1,3. 0 Hz), 4.78 (dd, 1H, J= 7.2, 3.7 Hz), 4.67 (dd, 1H, J = 12. 1,3. 7 Hz). 13C NMR (CDC13) 8 : 166.1, 165.4, 165.1, 151.9, 151.1, 147.1, 143.7- 140. 3 (C-F-coupling), 133. 8, 133. 7, 133. 6,129. 8,129. 8,129. 7,129. 3,128. 7,128. 7, 128. 6, 128.5, 128.4, 109.5-109. 1 (C-C-F-coupling), 108.3-108. 1 (C-C-F-coupling), 86. 3,80. 6,73. 9, 71.4, 63.6. MS (M+H): 616.1, observed: 616.1.

Reference： [1]Nucleosides, nucleotides and nucleic acids,2004,vol. 23,p. 161 - 170
[2]Patent: WO2005/16878,2005,A2 .Location in patent: Page/Page column 12-13
[3]Journal of the American Chemical Society,2008,vol. 130,p. 13639 - 13648

26
[ 6974-32-9 ]
[ 452-06-2 ]
C₃₁H₂₅N₅O₇ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 173 - 179

27
[ 6974-32-9 ]
[ 443-72-1 ]
[ 71118-16-6 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 173 - 179

28
[ 6974-32-9 ]
[ 134-58-7 ]
[ 38874-35-0 ]

Yield	Reaction Conditions	Operation in experiment
57%	With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 80℃; for 1h;Inert atmosphere;	To a suspension of <strong>[134-58-7]8-<strong>[134-58-7]azaguanine</strong></strong> (980 mg, 6.44 mmol) in dry ACN (27.0 mL) under argon was added sequentially N,0-bis(trimethylsilyl)acetamide (3.93 g, 19.3 mmol), [(2R,3R,4R,5,S)-5-acetoxy-3,4-dibenzoyloxy-tetrahydrofuran-2-yl]methyl benzoate (3.56 g, 7.06 mmol) and trimethylsilyl trifluoromethanesulfonate (2.86 g, 12.9 mmol). The reaction mixture was allowed to stir at rt for 15 min and then heated at 80 C for 1 h. The reaction mixture was allowed to cool to rt and the solvents were evaporated. The residue was partitioned between EtOAc and sat. NaHC03 solution and the phases were separated. The organic phase was washed with water and brine, dried over Na2S04, filtered and concentrated. The residue was adsorbed onto Celite. The crude mixture was purified by silica gel chromatography (0-7% MeOH / DCM) to provide [(2R,3R,4R,5R)-5-(5-amino-7-oxo-6H-triazolo[4,5-d]pyrimidin-3-yl)-3,4- dibenzoyloxy-tetrahydrofuran-2-yl]methyl benzoate as a yellow solid (2.30 g, 57%). LCMS (AA): m/z = 597.2 (M+H).

Reference： [1]Patent: WO2019/92660,2019,A1 .Location in patent: Paragraph 0461
[2]Journal of Organic Chemistry,2007,vol. 72,p. 173 - 179

29
[ 6974-32-9 ]
[ 938-55-6 ]
[ 70230-70-5 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 173 - 179

30
[ 6974-32-9 ]
[ 5098-11-3 ]
[ 17289-59-7 ]
[ 23192-64-5 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 173 - 179

31
[ 6974-32-9 ]
[ 5098-11-3 ]
C₃₀H₂₄N₄O₇ [ No CAS ]
[ 70590-21-5 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 173 - 179

32
[ 6974-32-9 ]
[ 4928-88-5 ]
[ 39030-43-8 ]
[ 36791-04-5 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 173 - 179

33
[ 6974-32-9 ]
[ 18672-03-2 ]
C₃₃H₂₅Cl₂N₃O₇ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 173 - 179

34
[ 6974-32-9 ]
[ 272-97-9 ]
[ 26884-45-7 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 173 - 179

35
[ 6974-32-9 ]
[ 23616-31-1 ]
[ 444898-55-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 562 - 565

36
[ 6974-32-9 ]
[ 131002-09-0 ]
[ 444898-43-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 562 - 565

37
[ 6974-32-9 ]
[ 26956-43-4 ]
[ 444898-86-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 562 - 565

38
[ 6974-32-9 ]
[ 223671-15-6 ]
[ 444898-46-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 562 - 565

39
[ 6974-32-9 ]
[ 82827-09-6 ]
[ 444898-85-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 562 - 565

40
[ 6974-32-9 ]
2-hydroxy-7-benzyloxycarbonyl-7H-pyrrolo[2,3-d]pyrimidine [ No CAS ]
[ 937162-93-1 ]

Yield	Reaction Conditions	Operation in experiment
45%		To a solution of the compound 4 (143 mg, 0.53 mmol) in CH3CN (10 mL) was added N,O-bis (trimethylsilyl) acetamide (0.26 ml, 1.1 mmol). The reaction mixture was stirred at 80 C for 20 min and cooled down to room temperature. To the mixture were added 2,3, 5-TRI-O-BENZOYL-1-O-ACETYL-P-D-RIBOFURANOSE (5A) (320 mg, 0.63 mmol) and SnCl4 (0. 85 mL, 0.84 MMOL). The reaction mixture was stirred at 90 C for 2 h, cooled down to room temperature and diluted with CH2C12 (100 mL). The organic solution was washed with aqueous NAHCO3 solution (100 mL) and brine (100 mL), dried with NA2S04, and concentrated to dryness. Silica gel CHROMATOGRAPHY (CH2CL2 : MeOH = 95: 5) yielded 138 mg of the target compound (45%). 1H NMR (CDCl3) : 86. 60 (D, J = 3.0 Hz, 1H, H-1').

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5261 - 5264
[2]Patent: WO2004/80466,2004,A1 .Location in patent: Page/Page column 33

41
[ 6974-32-9 ]
[ 4331-29-7 ]
[ 20649-47-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 6239 - 6244

42
[ 6974-32-9 ]
trimethylsilylated N-(dimethylaminomethylene)guanine [ No CAS ]
[ 1867-73-8 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 173 - 179

43
[ 6974-32-9 ]
trimethylsilylated N-(dimethylaminomethylene)guanine [ No CAS ]
[ 1818-71-9 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 173 - 179

44
[ 6974-32-9 ]
trimethylsilylated N-(dimethylaminomethylene)guanine [ No CAS ]
[ 7724-76-7 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 173 - 179

45
[ 6974-32-9 ]
4-methylbenzimidazole N-trimethylsilyl derivative [ No CAS ]
[ 36791-04-5 ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2004,vol. 23,p. 715 - 724

46
[ 6974-32-9 ]
thioether-bound (4-hydroxypyrimidine-2-yl)-Merrifield resin [ No CAS ]
[ 4291-63-8 ]

Reference： [1]European Journal of Organic Chemistry,2003,p. 3997 - 4002

47
[ 6974-32-9 ]
[ 3056-17-5 ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 7267 - 7272

48
[ 6974-32-9 ]
[ 3690-10-6 ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 1597 - 1600

49
[ 6974-32-9 ]
[ 2627-69-2 ]

Reference： [1]Journal of Organic Chemistry,1985,vol. 50,p. 747 - 754
[2]Journal of Organic Chemistry,1985,vol. 50,p. 747 - 754

50
[ 6974-32-9 ]
[ 22224-41-5 ]

Yield	Reaction Conditions	Operation in experiment
65.1%	With hydrogenchloride; In dichloromethane; for 2.5h;Cooling with ice;	The synthesis of compound vi: The compound v (2.57mmol) was dissolved in 26 ml dry dichloromethane and dry HCl gas was slowly introduced into an ice-water bath for 2.5 hours. The solution was washed with 19.5ml ice water and the organic layer was separated. The organic layer was washed with saturated sodium bicarbonate until the water layer shows weak alkaline, and then washed with ice water until the water layer shows neutral, dried over anhydrous sodium sulfate for more than 4 hours, and then drawn off under a reduced pressure to obtain light yellow syrup. The syrup was recrystallized using the mixed solvent of hexane and dichloromethane, so as to obtain the white solid compound vi (65.1%). 1H NMR(CDCl3) deltappm: 7.36?8.14 (m, 15H, OBz), 6.68 (d, J=4.4Hz, 1H, H-1), 5.59 (dd, 1H, H-3), 4.64?4.80 (m, 4H, H-2, H-4 and H-5). M,p, 139?140C.

Reference： [1]Patent: EP2177527,2010,A1 .Location in patent: Page/Page column 11
[2]Journal of Organic Chemistry,1985,vol. 50,p. 2597 - 2598

51
[ 6974-32-9 ]
[ 36791-04-5 ]

Reference： [1]Chemische Berichte,1981,vol. 114,p. 1234 - 1255

52
[ 6974-32-9 ]
[ 1094-61-7 ]

Reference： [1]Synthesis,1981,p. 388 - 389
[2]Journal of the Chemical Society,1957,p. 3727,3731

53
[ 6974-32-9 ]
[ 1122-28-7 ]
[ 94619-73-5 ]

Reference： [1]Patent: EP1227103,2002,A2 .Location in patent: Example 4, A

54
[ 6974-32-9 ]
[ 28128-30-5 ]
[ 859211-32-8 ]

Yield	Reaction Conditions	Operation in experiment
75%	With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 20 - 27℃; for 4.16667h;	Preparation of 9-(2'*3'n5'-tri-O-benzoyl-ss-D-ribofuranosyl .-2-methoxyadenine; A mixture of 2-methoxyadenine (11 g, 68 mmol) and 1-O-acetyl-2, 3, 5-tri-O-benzoyl-ss-D- ribofuranose (41 g, 81 mmol) was dried by co-evaporation with anhydrous acetonitrile (2 x 60 mL). To this mixture in anhydrous acetonitrile (328 ml) was added dropwise, trimethylsilyl trifluoromethylsulfonate (29 ml, 36 g, 162 mmol) over 10 minutes (a small exotherm was noted 24-27C). The suspended material is noted to be gradually solvated during addition. On completion of addition, the reaction mixture was stirred at ambient temperature for 4 h. The reaction mixture was then diluted with dichloromethane (328 mL) and washed with 1N aq. sodium hydroxide (200 mL) and brine (200 mL). The organic phase was dried with magnesium sulfate (20g) and filtered. The solution was then concentrated under reduced pressure to approximately a quarter of its original volume at which point a precipitate started to form. After standing for 1 h the precipitate was filtered and the filter cake washed with methyl t-butyl ether (2 x 100mL). The solid was dried at room temperature to give 9-(2', 3', 5'-tri-O-benzoyl-ss-D-ribofuranosyl)-2-methoxyadenine (31g, 75 mol%) as a white solid.

Reference： [1]Patent: WO2005/70947,2005,A1 .Location in patent: Page/Page column 14

55
[ 6974-32-9 ]
[ 905581-73-9 ]

Yield	Reaction Conditions	Operation in experiment
60%		Step e: (2R,3R,4R,5-R)-2-r(benzoyloxy)methyn-5-{4-r(lS)-2)3-dihydro-lH-inden-l- ylamino1-lH-imidazor4,5-clpyridin-l-yl}tetrahydrofuran-3,4-diyl dibenzoate; [0937] To a solution of N-[(lS)-2,3-dmydro-lH-inden-l-yl]-lH-imidazo[4,5- c]pyridin-4~amine (160 mg, 0.64 mmol) in AcCN (5 mL) was added N,O- bis(trimethylsilyl)acetamide (474 muL, 1.92 mmol) dropwise to obtain a clear solution which was refluxed for lOmin. The solution was allowed to cool to r.t and l-O-acetyl-2,3,5-tri-O- benzoyl-beta-D-ribofuranose (322 mg, 0.64 mmol) was added as a solution in AcCN (3 mL). Trimethylsilyl trifluoromethanesulfonate (115 muL, 0.64 mmol) was added dropwise and the reaction was heated at reflux for 3h. The reaction was quenched with MeOH, concentrated, and the residue was purified by flash chromatography (0 to 25% DCM/EtOAc) to obtain the product as a white solid (266mg, 60%).[0938] LCMS: R.t = 1.63 min, ES+ 695 (formic acid).

Reference： [1]Patent: WO2006/84281,2006,A1 .Location in patent: Page/Page column 188

56
[ 6974-32-9 ]
[ 4928-88-5 ]
[ 39925-12-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	With toluene-4-sulfonic acid; In methanol;	EXAMPLE 10 A mixture of methyl 1,2,4-triazole-3-carboxylate (1.27 g, 0.01 mole) and 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (5.04 g, 0.01 mole) was melted and then 0.095 g of p-toluenesulfonic acid was added thereto. The reaction mixture was reacted for 3 hours, while maintaining the temperature of the reaction mixture at 95+-5° C. And then, the reaction mixture was crystallized with 25 ml of methanol to give 4.85 g of 1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-<strong>[4928-88-5]1,2,4-triazole-3-carboxylic acid methyl ester</strong> (yield: 85percent). NMR (CDCl3) delta (ppm): 3.96(d, 3H), 4.67-4.80(m, 2H), 4.87(m, 1H), 6.11(t, 1H), 6.16(q, 1H), 6.34(d, 1H), 7.38-8.07(m, 15H), 8.44(s, 1H)

Reference： [1]Patent: US2003/120064,2003,A1

57
[ 6974-32-9 ]
[ 1122-28-7 ]
hexamethyldisilazane (HMDS) [ No CAS ]
chlorotrimethylsilane (CTMS) [ No CAS ]
trifluoromethanesulfonic acid (TFMSA) [ No CAS ]
[ 94619-73-5 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; acetonitrile;	(a) 1-(2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl)-<strong>[1122-28-7]4,5-dicyanoimidazole</strong> A solution of <strong>[1122-28-7]4,5-dicyanoimidazole</strong> (354 mg, 3.0 mmol) and 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (1.51 g, 3 mmol) in acetonitrile (30 mL) was charged to a flame-dried, three-necked, 50-mL round-bottomed flask, equipped with a refluxing condenser, a magnetic stirrer, and a N2 gas inlet. The solution was stirred in an ice-water bath for 5 minutes. Freshly distilled hexamethyldisilazane (HMDS) (0.7 mL, 3.3 mmol), freshly distilled chlorotrimethylsilane (CTMS) (0.45 mL, 3.6 mmol), and trifluoromethanesulfonic acid (TFMSA) (0.3 mL, 3.6 mmol) were consecutively added to the above solution. The resulting solution was stirred in an ice-water bath for 30 minutes. The reaction, as monitored by TLC (silica gel, toluene:acetic acid:water=5:5:1), showed complete conversion to the product in 30 minutes. Methylene chloride (30 mL) was added to the reaction mixture and was extracted with saturated aqueous NaHCO3. The organic layer was separated, and the aqueous layer was once again extracted with CH2 Cl2 (10 mL). The combined organic extracts were washed with saturated aqueous NaCl, dried over anhydrous MgSO4, filtered, and the filtrate was evaporated to dryness under reduced pressure to obtain a foam. Yield 1.5 g (94%), mp 68-72 C: 1 H NMR (DMSO-d6) delta 8.68 (s, 1 H, imidazole CH), 7.92 (m, 5 H, Ph-H), 7.63 (m, 5 H, Ph-H), 7.40 (m, 5 H, Ph-H), 6.63 (d, J=4.8 Hz, 1 H, H-1'), 6.06 (t, J=5.1 Hz, 1 H, H-2'), 5.99 (t, 1 H, H-3'), 4.97 (q, 1 H, H-4'), 4.74 (dd, 2 H, H-5'); 13 C NMR (DMSO-d6) delta 163 (C=O), 161 (C=O), 160.5 (C=O), 142.6 (imidazole CH), 135 (Ph-C), 134.8 (Ph-C), 134.4 (Ph-C), 130.4 (Ph-C), 130.2 (Ph-C), 130.0 (Ph-C), 129.8 (Ph-C), 129.7 (Ph-C), 129.5 (Ph-C), 129.4 (Ph-C), 129.3 (Ph-C), 129.0 (Ph-C), 124 (C=C), 113 (C N), 111.7 (C N), 109.2 (C=C), 89.8 (C-1'), 81.8 (C-2'), 75.5 (C-3'), 71.5 (C-4'), 64.2 (C-5'). Anal. Calcd. for C31 H22 N4 O7: C, 66.19; H, 3.94; N, 9.96. Found: C, 66.20; H, 3.96; N, 9.76.
	In dichloromethane; acetonitrile;	(a) 1-(2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl)-<strong>[1122-28-7]4,5-dicyanoimidazole</strong> A solution of <strong>[1122-28-7]4,5-dicyanoimidazole</strong> (354 mg, 3.0 mmol) and 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (1.51 g, 3 mmol) in acetonitrile (30 mL) was charged to a flame-dried, three-necked, 50-mL round-bottomed flask, equipped with a refluxing condenser, a magnetic stirrer, and a N2 gas inlet. The solution was stirred in an ice-water bath for 5 minutes. Freshly distilled hexamethyldisilazane (HMDS) (0.7 mL, 3.3 mmol), freshly distilled chlorotrimethylsilane (CTMS) (0.45 mL, 3.6 mmol), and trifluoromethanesulfonic acid (TFMSA) (0.3 mL, 3.6 mmol) were consecutively added to the above solution. The resulting solution was stirred in an ice-water bath for 30 minutes. The reaction, as monitored by TLC (silica gel, toluene:acetic acid:water =5:5:1), showed complete conversion to the product in 30 minutes. Methylene chloride (30 mL) was added to the reaction mixture and was extracted with saturated aqueous NaHCO3. The organic layer was separated, and the aqueous layer was once again extracted with CH2Cl2 (10 mL). The combined organic extracts were washed with saturated aqueous NaCl, dried over anhydrous MgSO4, filtered, and the filtrate was evaporated to dryness under reduced pressure to obtain a foam. Yield 1.5 g (94%), mp 68-72 C.: 1H NMR (DMSO-d6) delta 8.68 (s, 1H, imidazole CH), 7.92 (m, 5H, Ph-H), 7.63 (m, 5H, Ph-H), 7.40 (m, 5H, Ph-H), 6.63 (d, J=4.8 Hz, 1H, H-1'), 6.06 (t, J=5.1 Hz, 1H, H-2'), 5.99 (t, 1H, H-3'), 4.97 (q, 1H, H-4'), 4.74 (dd, 2H, H-5'); 13C NMR (DMSO-d6) delta 163 (C=O), 161 (C=O), 160.5 (C=O), 142.6 (imidazole CH), 135 (Ph-C), 134.8 (Ph-C), 134.4 (Ph-C), 130.4 (Ph-C), 130.2 (Ph-C), 130.0 (Ph-C), 129.8 (Ph-C), 129.7 (Ph-C), 129.5 (Ph-C), 129.4 (Ph-C), 129.3 (Ph-C), 129.0 (Ph-C), 124 (C=C), 113 (C?N), 111.7 (C?N), 109.2 (C=C), 89.8 (C-1'), 81.8 (C-2'), 75.5 (C-3'), 71.5 (C-4'), 64.2 (C-5'). Anal. Calcd. for C31H22N4O7: C, 66.19; H, 3.94; N, 9.96. Found: C, 66.20; H, 3.96; N, 9.76.

Reference： [1]Patent: US5843912,1998,A
[2]Patent: US6677310,2004,B1

58
[ 6974-32-9 ]
[ 645-15-8 ]
[ 4967-77-5 ]
[ 41086-74-2 ]
[ 31843-61-5 ]

Yield	Reaction Conditions	Operation in experiment
		Methyl 1,2,3-triazole-4-carboxylate (2.54 g, 0.020 mol) and 1-O-acetyl- 2,3,5-tri-O-benzoyl-beta -D-ribofuranosyl (10.1 g, 0.020 mol) and 1-0-acetyl-2,3,5-tri-0-benzoyl-beta-D-ribofuranose (10.1 g, 0.020 mol) were thoroughly mixed in a mortar, then heated in an oil bath at 160° until a melt was achieved. <strong>[645-15-8]Bis-(p-nitrophenyl)phosphate</strong> (5 mg) was added and heating in vacuo at 160°-165° was continued for 10 minutes. The residue was triturated with benzene and the insoluble product was collected and recrystallized from benzene to yield 3.00 g of 2, m.p. 189°-190°, which was identical with an authentic sample prepared by cycloaddition of the azido sugar with methyl propiolate as reported by Alonso, et al. J Heterocyclic Chem., 7, 1269 (1970). The filtrate was evaporated to a syrup and the residue was crystallized from methanol to provide 3.83 g of 1: m.p. 112°-113°; [alpha]D25 -57.6° (c 1.00, chloroform); nmr (DMSO-d6) delta 6.87 (d, 1, J1',2' 2.2 Hz, 1'--H), 8.50 (s, 1, 5--H); (CDCl3) delta 6.59 (d, 1, J1',2' 1.3 Hz, 1'--H), 8.12 (s, 1, 5--H). Anal. Calcd for C30 H25 N3 O9: C, 63.04; H, 4.41; N, 7.35. Found: C, 63.00; H, 4.46; N, 7.12.

Reference： [1]Patent: US3968103,1976,A

59
[ 6974-32-9 ]
[ 645-15-8 ]
[ 4928-88-5 ]
[ 39925-12-7 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 2 1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxylic acid methyl ester (fusion procedure) A mixture of methyl 1,2,4-triazole-3-carboxylate (12.7 g., 100 mmole) and 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (55.4 g., 110 mmole) was heated in an oil bath maintained at 160-165°. After the sugar had melted, bis(p-nitrophenyl) phosphate (400 mg.) was added with stirring and the mixture was heated under diminished pressure at 160-165° for 15-20 min. Crystallization of the residue from ethyl acetate-ethanol provided 42.5 g. (74.5percent) of product with M.P. 137-139°.

Reference： [1]Patent: US29835,1978,E1

60
[ 6974-32-9 ]
[ 61948-86-5 ]
C₃₅H₂₈N₂O₁₀ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 17605 - 17614

61
[ 6974-32-9 ]
[ 52523-35-0 ]
[ 320-67-2 ]

Yield	Reaction Conditions	Operation in experiment
71%		Example 2 Coupling of Silyl 5-Azacytosine to Sugar and Deprotection A mixture of 2-[(trimethylsilyl)amino]-4-[(trimethylsilyl)oxy]-s-triazine (4.5 Kg), 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (8.8 Kg), anhydrous MeCN (34.6 Kg) and TfOH (600 g) were heated at 55 C. for 12.5 hours. The reaction mixture was cooled to 45 C., DMSO (29 Kg) was added, and the MeCN was evaporated at an internal temperature of <50 C. under vacuum until about 54 L of the solution. The solution was cooled to 23 C. MeOH (13.9 Kg) was added followed by a solution of 30% NaOMe in MeOH solution (2.5 Kg) that was pre-diluted with MeOH (7.0 Kg). The solution was stirred at 23 C. for 35 minutes. When the reaction was complete MeOH (90.4 Kg) was added and the resulting slurry was stirred at 22 C. for 3 hours and 10 minutes and was then filtered and washed three times with MeOH (7.0 Kg each). The cake was dried under vacuum at below 70 C. for 9 hours and 20 minutes to give 3.2 Kg of 98.89% purity crude azacitidine (71% yield based on 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose).

Reference： [1]Patent: US2010/36112,2010,A1 .Location in patent: Page/Page column 7

62
[ 6974-32-9 ]
[ 123148-78-7 ]
[ 480439-89-2 ]

Yield	Reaction Conditions	Operation in experiment
63%	With trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20 - 80℃; for 17.5h;	To a suspension of MM (6.7 g, 24.0 mmol) and JJ (12 g, 24.0 mmol) in anhydrous acetonitrile (240 ml) was added DBU (5.4 ml, 36.0 mmol). The mixture was then treated with TMSOTf (8.7 ml, 48.0 mmol). The mixture was stirred at room temperature for 30 min and then heated at 80 C for 17 h. The mixture was cooled to room temperature. A saturated aqueous NaHCO3 solution (250 ml) was added to the reaction mixture and extracted with EtOAc (2 x 200 ml). The organics were dried over Na2SO4 and concentrated to give orange residue. The orange residue was triturated with methanol to give brown solid. The brown solid was dissolved in minimal amount OfCH2Cl2 and loaded onto a column packed with silica/CH2Cl2 and eluted with CH2Cl2 /EtOAc (2:1). The fractions containing the required product were collected and concentrated to afford (2R,3R,4R,5R)-2- (benzoyloxymethyl)-5-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)tetrahydrofuran- 3,4-diyl dibenzoate as off-white solid (10.9 g, 63%). LC/MS m/z 724 (M+H).
4.51 g	With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; for 2h;Reflux;	To a stirred suspension of pyrimidine S21 (2.89 g, 10.4 mmol) in 52 mL of CH3CN was added BSA (2.79 mL, 11.42mmol). The solution was stirred for 10 minutes during which time the reaction mixture became homogenous. 1-OAcetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (5.75 g, 11.4 mmol) was added followed by TMSOTf (2.15 mL, 11.4mmol), and the reaction was heated to reflux for 2 h before being cooled to rt and diluted with 100 mL of EtOAc. The organic layer was washed with 100 mL of satd. NaHCO3 and 100 mL of brine. The organic layer was dried(Na2SO4), filtered, and concentrated in vacuo to afford a yellow oil. The oil was purified by flash chromatography(40% EtOAc/Hexanes) to afford the riboside 42

Reference： [1]Synthetic Communications,2012,vol. 42,p. 358 - 374
[2]Organic and Biomolecular Chemistry,2015,vol. 13,p. 68 - 72
[3]Patent: WO2010/135520,2010,A1 .Location in patent: Page/Page column 130-131
[4]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 5433 - 5440
[5]European Journal of Medicinal Chemistry,2020,vol. 188

63
[ 6974-32-9 ]
[ 79607-23-1 ]
[ 224175-70-6 ]

Reference： [1]Archiv der Pharmazie,2013,vol. 346,p. 757 - 765
[2]Tetrahedron,2011,vol. 67,p. 7336 - 7342

64
[ 6974-32-9 ]
[ 208580-23-8 ]
[ 224175-69-3 ]

Reference： [1]Tetrahedron,2011,vol. 67,p. 7336 - 7342

65
[ 6974-32-9 ]
[ 461-89-2 ]
[ 1627-29-8 ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2011,vol. 30,p. 227 - 234

66
[ 6974-32-9 ]
[ 55018-48-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylsilane; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 20℃;Inert atmosphere;	Trimethylsilyl trifluoromethanesulfonate (7.2 mL, 40.0 mmol) was added to a solution of 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (10.1 g, 20.0 mmol) and triethylsilane (9.6 mL, 60.0 mmol) in MeCN (20 mL), and then the mixture was stirred at room temperature for 24 h. The mixture was partitioned between EtOAc and saturated aqueous NaHCO3 solution. The organic layer was wash with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane/EtOAc, 15:1~12:1) to give 2,3,5-tri-O-benzoyl-1-deoxy-D-ribofuranose as a colorless oil (8.9 g, quant).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2518 - 2521

67
[ 6974-32-9 ]
[ 1221177-84-9 ]
[ 1374429-99-8 ]

Yield	Reaction Conditions	Operation in experiment
54%		3.9.4,6-Dichloro-9-(2,3,5-tri-O-benzoyl-beta-d-ribofuranosyl)-pyrimido[4,5-b]indole (13): Pyrimidoindole 11 (200 mg, 0.84 mmol) was suspended in acetonitrile (5 ml) and BSA (206 mul, 0.84 mmol) was added. Reaction mixture was stirred for 10 min at rt., TMSOTf (308 mul, 1.68 mmol) and protected ribofuranose (430 mg, 0.84 mmol) were added. Mixture was heated to 60 C for 8 h. After cooling to rt, the mixture was extracted with EtOAc and water, organic layer was washed with NaHCO3 and again with water, dried over MgSO4 and evaporated under reduced pressure. Crude product was purified using column chromatography (hexane/EtOAc, 0-40% EtOAc). After crystallization from chloroform/methanol mixture, nucleoside 13 (572 mg, 54%) was observed as white crystals; mp: 164-165 C. IR (ATR): nu = 1722, 1545, 1472, 1433, 1292, 1266, 1119, 1098, 714 cm-1. 1H NMR (600.1 MHz, DMSO-d6):): 4.68 (dd, 1H, Jgem = 12.4, J5'b,4' = 4.3, H-5'b); 4.85 (dd, 1H, Jgem = 12.4, J5'a,4' = 3.2, H-5'a); 4.90 (ddd, 1H, J4',3' = 6.6, J4',5' = 4.3, 3.2, H-4'); 6.36 (t, 1H, J3',2' = J3',4' = 6.6, H-3'); 6.59 (dd, 1H, J2',3' = 6.6, J2',1' = 4.4, H-2'); 7.02 (d, 1H, J1',2' = 4.4, H-1'); 7.42 (m, 2H, H-m-Bz-2'); 7.49 (m, 4H, H-m-Bz-3',5'); 7.60 (dd, 1H, J7,8 = 9.1, J7,5 = 2.2, H-7); 7.62 (m, 1H, H-p-Bz-2'); 7.68 (m, 2H, H-p-Bz-3',5'); 7.84 (m, 2H, H-O-Bz-2'); 7.91 (m, 2H, H-O-Bz-5'); 7.99 (m, 2H, H-o-Bz-3'); 8.15 (dd, 1H, J8,7 = 9.1, J8,5 = 0.5, H-8); 8.28 (dd, 1H, J5,7 = 2.2, J5,8 = 0.5, H-5); 8.81 (s, 1H, H-2). 13C NMR (150.9 MHz, DMSO-d6): 63.1 (CH2-5'); 70.3 (CH-3'); 72.5 (CH-2'); 78.9 (CH-4'); 86.4 (CH-1'); 111.7 (C-4a); 114.0 (CH-8); 119.4 (C-4b); 122.0 (CH-5); 128.6, 128.8 (C-i-Bz); 128.9 (CH-7); 128.9, 128.9, 129.0 (CH-m-Bz); 129.3 (CH-o-Bz-5'); 129.3 (C-i-Bz); 129.5 (CH-O-Bz-2'); 129.6 (CH-O-Bz-3'); 133.8, 134.1 (CH-p-Bz); 137.1 (C-8a); 152.7 (C-4); 154.6 (CH-2); 155.5 (C-9a); 164.8 (COPh-2'); 165.0 (COPh-3'); 165.5 (COPh-5'). ESI MS m/z (rel.%): 682 (100) [M+H], 684 (66) [M+2+H], 686 (26) [M+4+H]. HR MS (ESI) for C36H26Cl2N3O7 [M+H]: calcd 682.11480; found 682.11423; for C36H25Cl2N3O7Na [M+Na]: Calcd 704.09660; found 704.09618.

Reference： [1]Bioorganic and medicinal chemistry,2012,vol. 20,p. 6123 - 6133,11

68
[ 6974-32-9 ]
[ 5719-08-4 ]
[ 1403589-26-3 ]

Yield	Reaction Conditions	Operation in experiment
46%		3.9. 4,6-Dichloro-9-(2,3,5-tri-O-benzoyl-b-D-ribofuranosyl)-pyrimido[4,5-b]indole (13) : Pyrimidoindole 11 (200 mg, 0.84 mmol) was suspended in acetonitrile (5 ml) and BSA (206 ll, 0.84 mmol) was added. Reaction mixture was stirred for 10 min at rt., TMSOTf (308 ll, 1.68 mmol) and protected ribofuranose (430 mg, 0.84 mmol) were added. Mixture was heated to 60 C for 8 h. After cooling to rt, the mixture was extracted with EtOAc and water, organic layer was washed with NaHCO3 and again with water, dried over MgSO4 and evaporated under reduced pressure. Crude product was purified using column chromatography (hexane/EtOAc, 0-40% EtOAc). After crystallization from chloroform/methanol mixture, nucleoside 13 (572 mg, 54%) was observed as white crystals; 3.10 4-Chloro-9-(2,3,5-tri-O-benzoyl-beta-d-ribofuranosyl)-pyrimido[4,5-b]indole (14) : Compound 14 was prepared as described for 13 from pyrimidoindole 12 (300 mg, 1.5 mmol) to give 440 mg (46%) of white crystals; mp 178-182 C, IR (ATR): nu = 2360, 2336, 1718, 1546, 1442, 1261, 1090, 1068, 704 cm-1. H NMR (600.1 MHz, DMSO-d6): 4.69 (dd, 1H, Jgem = 12.4, J5'b,4' = 4.2, H-5'b); 4.85 (dd, 1H, Jgem = 12.4, J5'a,4' = 3.2, H-5'a); 4.91 (ddd, 1H, J4',3' = 6.6, J4',5' = 4.2, 3.2, H-4'); 6.36 (t, 1H, J3',2' = J3',4' = 6.6, H-3'); 6.61 (dd, 1H, J2',3' = 6.6, J2',1' = 4.6, H-2'); 7.03 (d, 1H, J1',2' = 4.6, H-1'); 7.41 (m, 2H, H-m-Bz-2'); 7.50 (m, 4H, H-m-Bz-3',5'); 7.51 (ddd, 1H, J6,5 = 7.8, J6,7 = 7.3, J6,8 = 1.0, H-6); 7.57 (ddd, 1H, J7,8 = 8.4, J7,6 = 7.3, J7,5 = 1.3, H-7); 7.62 (m, 1H, H-p-Bz-2'); 7.68 (m, 2H, H-p-Bz-3',5'); 7.84 (m, 2H, H-o-Bz-2'); 7.93 (m, 2H, H-o-Bz-5'); 7.99 (m, 2H, H-o-Bz-3'); 8.10 (ddd, 1H, J8,7 = 8.4, J8,6 = 1.0, J8,5 = 0.7, H-8); 8.35 (ddd, 1H, J5,6 = 7.8, J5,7 = 1.3, J5,8 = 0.7, H-5); 8.78 (s, 1H, H-2). 13C NMR (150.9 MHz, DMSO-d6): 63.1 (CH2-5'); 70.3 (CH-3'); 72.2 (CH-2'); 78.8 (CH-4'); 86.2 (CH-1'); 112.1 (CH-8); 112.4 (C-4a); 118.0 (C-4b); 122.9 (CH-5); 123.3 (CH-6); 128.6, 128.8 (C-i-Bz); 128.9 (CH-m-Bz); 129.0 (CH-7); 129.3 (CH-o-Bz-5'); 129.4 (C-i-Bz); 129.5 (CH-o-Bz-2'); 129.6 (CH-o-Bz-3'); 133.8, 134.1 (CH-p-Bz); 138.4 (C-8a); 152.1 (C-4); 154.0 (C-2-furyl); 154.0 (CH-2); 155.3 (C-9a); 164.8 (COPh-2'); 165.0 (COPh-3'); 165.5 (COPh-5'). ESI MS m/z (rel.%): 670 (100) [M+Na], 672 (33) [M+2+Na]. HR MS (ESI) for C36H27ClN3O7 [M+H]: calcd 648.15320; found 648.15318.

Reference： [1]Bioorganic and medicinal chemistry,2012,vol. 20,p. 6123 - 6133,11

69
[ 6974-32-9 ]
[ 69099-99-6 ]
[ 122336-54-3 ]

Yield	Reaction Conditions	Operation in experiment
70%		5-Nitrocytosine, 7 (3 g, 19.23 mmol) was suspended in HMDS (40 mL, 191.8 mmol) containing TMS-Cl (1 mL, 7.82 mmol). The mixture was heated under reflux for 36 h and then concentrated in vacuo. To this crude material was added beta-D-ribofuranose-1-acetate-2,3,5-tribenzoate (9.737 g, 19.30 mmol) and the material was suspended in MeCN (125 mL). The suspension was degassed with N2, then SnCl4 (23 mL in 1 M solution in CH2Cl2) was added. The suspension quickly turned clear and then the solution was stirred for 3 h at room temperature. Distilled water (100 mL) was added with vigorous stirring to hydrolyze the remaining SnCl4. This facilitated the precipitation of the product. The solid was collected, suspended in EtOAc (500 mL) and washed with aq Na2CO3 (600 mL 4). The organic layer was diluted with EtOAc and washed with satd NaCl (700 mLx1) and H2O (700 mLx2). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The resulting solid was triturated with CHCl3 and dried in vacuo yielding 8 g of the product (70%). Mp 218-220 C decomp. (Reported mp 211-213 C decomp.).43 [alpha]D23 -101.3 (c 1.02, CHCl3). IR (ZnSe): nu 3480, 3366, 3060, 1716, 1684, 1653, 1601, 1589, 1583, 1491,1119,1418,1363, 1281, 1265, 1130, 1110,1093,1039,1069, 1048, 1024, 927, 891, 851, 819, 761, 736, 703 cm-1. 1H NMR (600 MHz, CDCl3): delta 9.08 (s, 1H), 8.27 (br s, 1H), 8.07 (d, J=6.2 Hz, 2H), 7.95 (s, 1H), 7.92-7.89 (m, 4H), 7.55-7.52 (m, 3H) 7.45-7.31 (m, 6H), 6.33 (d, J=2.1 Hz, 1H), 5.91-5.91 (m, 2H), 4.83-4.76 (m, 3H) ppm. 13C NMR (150 MHz, CDCl3) delta: 166.1, 165.2, 157.7, 151.8,146.4, 133.7, 133.7, 133.5, 129.9, 129.8, 129.7, 128.5, 120.2, 90.5, 81.2, 74.9, 70.9, 63.4 ppm. HRMS (MALDI-TOF) m/z: calculated for C30H24N4NaO10+: 623.138 (MNa+). Found: 623.140 (MNa+).

Reference： [1]Tetrahedron,2013,vol. 69,p. 3698 - 3705

70
[ 6974-32-9 ]
[ 22276-95-5 ]
[ 952429-11-7 ]

Yield	Reaction Conditions	Operation in experiment
64%		General procedure: N,O-Bis(trimethylsilyl)acetamide (488.2 mg, 586.8 muL, 2.40 mmol) was added to a suspension of 7-bromo-6-chloro-7-deazapurine (464.9 mg, 2.00 mmol) in 20 mL dry acetonitrile. Afterwards, the solution was stirred for 15 min at room temperature in an argon atmosphere,followed by the addition of 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-Dribofuranose(1.21 g, 2.40 mmol) and trimethylsilyl trifluoromethanesulfonate(533.4 mg, 434.4 muL, 2.40 mmol). The reaction mixture was heated for 2 h at 80 C under argon with vigorous stirring. After glycosylation, the solution was left to cool down and diluted with 400 mL ethyl acetate. The organic phase was sequentially washed twice with a saturated sodium hydrogen carbonate solution and brine. Subsequently, the organic layer was dried with magnesium sulfate and the solvent was removed under vacuum, to afford the crude nucleoside. Purification by column chromatography on silica gel with hexane/ethylacetate (2:1) as eluent yielded the product as colorless solid (864.0 mg,1.28 mmol, 64%). 1H NMR (300 MHz, DMSO-d6) delta 8.62 (1H, s), 8.32(1H, s), 8.00-7.84 (6H, m), 7.69-7.61 (3H, m), 7.54-7.40 (6H, m), 6.73(1H, d, J=5.0 Hz), 6.32-6.28 (1H, m), 6.16-6.11 (1H, m), 4.90-4.85(1H, m), 4.84-4.65 (2H, m); 13C NMR (75 MHz, DMSO-d6) delta 165.4,164.7, 164.5, 151.4, 151.0, 150.3, 134.0, 133.9, 133.6, 129.4, 129.4,129.3, 129.2, 129.2, 128.8, 128.6, 128.2, 114.9, 88.1, 86.6, 79.3, 73.5,70.6, 63.4; HRMS (ESI): m/z calcd for C32H24BrClN3O7 [M+H]+676.0481, found 676.0489.
63%		N,O-Bis(trimethylsilyl)acetamide (BSA, 0.56 mL, 2.27 mmol) was added to a stirred suspension of 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (480 mg, 2.06 mmol) in dry acetonitrile (15 mL). After stirring at rt for 10 min, 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-d-ribofuranose (1.16 g, 2.31 mmol) was added, followed by the addition of trimethylsilyl trifluoromethanesulfonate (0.41 mL, 2.25 mmol). The reaction mixture was stirred at rt for 15 min, after which the flask was transferred to a preheated 80 C oil bath. After stirring for 1 h at 80 C, the reaction mixture was cooled to rt and diluted with EtOAc (75 mL). The organic phase was sequentially washed with aqueous saturated NaHCO3 solution and brine, dried (Na2SO4), filtered, and concentrated under reduced pressure to afford the crude nucleoside. Purification by flash column chromatography (silica gel, 20-100% EtOAc/hexanes gradient) provided (1) as a colorless foam (870 mg, 63%). TLC (silica gel, hexanes/ethyl acetate 3:1): Rf = 0.45. LRMS (ESI): 677.3, 675.2 and 673.2 [M+H]+.
		A solution of 56b (20 g, 86 mmoi) in thy ACN (300 mL) under nitrogen was charged with iV,O-Bistrimethyisiiyi)acetamide (19.3 g, 95 mmol) then stirred at RT for 30 mm. The mixture was then charged with I -O-acetvl-2.3.5-tri-O-benzoyl-13-d-ribofiiranose (56c) (48.1 g, 78 mmol) and TMSOTf(21 g, 78 mmol) and stirred at RT for 30 mm. The mixture was then heated and stirred at 80 C for 5 h. The reaction mixture was cooled to RI, diluted with EtOAc (1 IL) washed with sat. sodium bicarbonate (ilL), brine (1 IL), dried over Na2SO4, and filtered. The filtrate was concentrated under reduced pressure and purified by FCC (Si02, 15% EtOAc in hexanes) to afford 56d (31.4 g, 40.1 mmol, 51% yield) as a white solid foam. LCMS purity:86.5%; LRMS (ES1) m/z caicd for [M+H]?: 676.05/678.05. Found: 676.05/678.05.

Reference： [1]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 1704 - 1713
[2]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 1787 - 1794
[3]European Journal of Organic Chemistry,2015,vol. 2015,p. 7550 - 7556
[4]Patent: WO2018/85833,2018,A2 .Location in patent: Paragraph 0354
[5]European Journal of Medicinal Chemistry,2020,vol. 188

71
[ 6974-32-9 ]
[ 144872-52-6 ]
1-[5-O-tert-butyldiphenylsilyl-3-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)2-deoxy-β-D-ribofuranosyl]-5-iodouracil [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%		General procedure: To a cold solution (0C) of 1-O-2,3,5-tri-O-benzoyl-beta-D-ribofuranose(484 mg, 0.96 mmol) in 1,2-dichloroethane (12 mL) under nitrogen, tintetrachloride (0.14 mL, 1.18 mmol) was added and the solution was kept at 0C for 10 minutes. After addition of 1-[5-O-tert-butyldiphenylsilyl-2-deoxy-beta-D-ribofuranosyl]-5-fluorouracil (387 mg, 0.8 mmol), the resulting solution was kept at 0C for 40 minutes. Then 10% aqueous solution of sodium bicarbonate(5 mL) was added and the suspension was stirred at 0C for 20 minutes.The suspension was diluted with methylene chloride (20 mL) and filtered through Hyflo Super Cel; the organic layer was separated, washed with water (10 mL), dried, and evaporated to dryness. The residue was purified by column chromatography on silica gel (50 g). The column was washed with methylene chloride (500 mL) and then eluted with 1%ethanol in methylenechloride to give the resulting product as foam. The yield was 446 mg (60%).

Reference： [1]Nucleosides, nucleotides and nucleic acids,2013,vol. 32,p. 510 - 528

72
[ 6974-32-9 ]
[ 75-89-8 ]
2,3,5-tri-O-benzoyl-1-O-(2,2,2-trifluoroethyl)-β-D-ribofuranose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -30℃; for 1.5h;	To a solution of 1-O-acethyl-2,3,5-O-tribenzoyl-b-D-ribofuranose (2.00 g, 3.97 mmol) in CH2Cl2 (20 mL) was added dropwiseTMSOTf (0.86 mL, 4.76 mmol) and 2,2,2-trifluoroethanol (0.28 mL,3.97 mmol) at 30 C. The mixture was stirred at 30 C for 1.5 hand quenched by using aqueous NaHCO3 (saturated). The mixturewas partitioned between CHCl3 and H2O. The organic layer waswashed with aqueous NaHCO3 (saturated) and brine, dried(Na2SO4), and concentrated. The residue was purified by columnchromatography (SiO2, 20% EtOAc in hexane) to give 18 (2.16 g,3.97 mmol, 100%): 1H NMR (400 MHz, CDCl3) d 3.90e4.15 (m, 2H),4.56 (dd, 1H, J 5.5 and 11.9), 4.70 (dd, 1H, J 4.2 and 12.4), 4.78(dd, 1H, J 5.5 and 11.0), 5.37 (s, 1H), 5.78 (d, 1H, J 5.0), 5.88 (dd,1H, J 5.0 and 7.4), 7.30e8.07 (m, 15H); 13C NMR (126 MHz, CDCl3)d 64.5, 64.6, 64.9, 71.9, 75.3, 79.9, 105.6, 128.5, 128.5, 128.6, 129.6,129.8, 129.8,129.9,133.4, 133.6, 133.7,165.2, 165.4, 166.2. Anal. Calcdfor C28H23F3O81/10H2O: C, 61.56; H, 4.28. Found: C, 61.38; H, 4.24.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 103,p. 460 - 472

73
[ 6974-32-9 ]
[ 64-17-5 ]
[ 52783-88-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -30℃; for 1.5h;	To a solution of 1-O-acethyl-2,3,5-O-tribenzoyl-b-D-ribofuranose (3.00 g, 5.95 mmol) in CH2Cl2 (30 mL) was added dropwiseTMSOTf (1.29 mL, 7.14 mmol) and ethanol (0.35 mL, 5.95 mmol) ate30 C. The mixture was stirred at 30 C for 1.5 h and quenchedby using aqueous NaHCO3 (saturated). The mixture was partitionedbetween CHCl3 and H2O. The organic layer was washed withaqueous NaHCO3 (saturated) and brine, dried (Na2SO4), andconcentrated. The residue was purified by column chromatography(SiO2, 20% EtOAc in hexane) to give 14 (2.91 g, 5.94 mmol, 100%): 1HNMR (400 MHz, CDCl3) d 1.18 (t, 3H, J 7.1), 3.54 (dq, 1H, J 6.8 and8.5), 3.84 (dq, 1H, J 6.9 and 11.9), 4.52 (dd, 1H, J 6.4 and 12.8),4.66e4.74 (m, 2H), 5.26 (s, 1H), 5.67 (d, 1H, J 4.6), 5.88 (dd, 1H,J 5.0 and 6.4), 7.25e8.11 (m, 15H); 13C NMR (126 MHz, CDCl3)d 15.0, 64.0, 65.0, 72.7, 75.8, 78.9, 105.4, 128.4, 128.6, 129.1, 129.4,129.8, 129.9, 133.2, 133.4, 133.5, 165.4, 165.5, 166.3. Anal. Calcd forC28H26O87/10H2O: C, 66.84; H, 5.49. Found: C, 66.86; H, 5.19.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 103,p. 460 - 472

74
[ 6974-32-9 ]
[ 71-23-8 ]
2,3,5-O-tribenzoyl-1-O-propyl-β-D-ribofuranose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -30℃; for 0.5h;	To a solution of 1-O-acethyl-2,3,5-O-tribenzoyl-b-D-ribofuranose (3.00 g, 5.95 mmol) in CH2Cl2 (30 mL) was added dropwiseTMSOTf (1.29 mL, 7.14 mmol) and 1-propanol (0.53 mL, 7.14 mmol)at 30 C. The mixture was stirred at 30 C for 30 min andquenched by using aqueous NaHCO3 (saturated). The mixture waspartitioned between CHCl3 and H2O. The organic layer was washedwith aqueous NaHCO3 (saturated) and brine, dried (Na2SO4), andconcentrated. The residue was purified by column chromatography(SiO2, 20% EtOAc in hexane) to give 15 (2.94 g, 5.83 mmol, 98%): 1HNMR (600 MHz, CDCl3) d 0.90 (t, 3H, J 7.6),1.55e1.59 (m, 2H), 3.42(dd, 1H, J 6.9 and 15.8), 3.74 (dd, 1H, J 6.8 and 14.4), 4.52e4.54(m, 1H), 4.69e4.72 (m, 2H), 5.25 (s, 1H), 5.68 (d, 1H, J 4.8), 5.87(dd, 1H, J 2.8 and 5.0), 7.31e8.07 (m, 15H); 13C NMR (151 MHz,CDCl3) d 10.5, 14.2, 21.0, 22.6, 60.4, 65.1, 70.1, 72.7, 75.6, 78.7, 105.5,128.3, 128.5, 129.0, 129.3, 129.7, 129.8, 129.8, 133.1, 133.3, 133.4.Anal. Calcd for C29H28O8: C, 69.04; H, 5.59. Found: C, 68.80; H, 5.58.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 103,p. 460 - 472

75
[ 6974-32-9 ]
[ 78-83-1 ]
2,3,5-O-tribenzoyl-1-O-(2-methylpropyl)-β-D-ribofuranose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -30℃; for 2.5h;	To a solution of 1-O-acethyl-2,3,5-O-tribenzoyl-b-D-ribofuranose (2.00 g, 3.97 mmol) in CH2Cl2 (20 mL) was added dropwiseTMSOTf (0.86 mL, 4.76 mmol) and 2-methyl-1-propanol (0.37 mL,3.97 mmol) at 30 C. The mixture was stirred at e30 C for 2.5 hand quenched by using aqueous NaHCO3 (saturated). The mixturewas partitioned between CHCl3 and H2O. The organic layer waswashed with aqueous NaHCO3 (saturated) and brine, dried(Na2SO4), and concentrated. The residue was purified by columnchromatography (SiO2, 20% EtOAc in hexane) to give 16 (2.02 g,3.90 mmol, 98%): 1H NMR (400 MHz, CDCl3) d 0.87e0.92 (m, 6H),1.80e1.87 (m, 1H), 3.21 (dd, 1H, J 6.9 and 9.2), 3.58 (dd, 1H, J 6.4and 9.2), 4.53 (dd, 1H, J 5.3 and 11.2), 4.66e4.73 (m, 2H), 5.24 (s,1H), 5.69 (d, 1H, J 4.6), 5.85 (dd, 1H, J 4.6 and 6.9), 7.25e8.12 (m,15H); 13C NMR (151 MHz, CDCl3) d 19.2, 19.3, 28.3, 64.1, 65.2, 70.9,71.9, 72.8, 75.1, 75.6, 78.7, 101.0, 105.7, 128.3, 128.3, 128.5, 129.0,129.3, 129.7, 129.8, 133.1,133.3,133.4,165.3, 165.4, 166.2. Anal. Calcdfor C30H30O87/10H2O: C, 67.84; H, 5.96. Found: C, 67.59; H, 5.73.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 103,p. 460 - 472

76
[ 6974-32-9 ]
[ 75-84-3 ]
[ 59556-71-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -30℃; for 3.5h;	To a solution of 1-O-acethyl-2,3,5-O-tribenzoyl-b-D-ribofuranose (3.00 g, 5.95 mmol) in CH2Cl2 (25 mL) was added dropwiseTMSOTf (1.29 mL, 7.14 mmol) and 2,2-dimethyl-1-propanol (0.52 g,5.95 mmol) in CH2Cl2 (5 mL) at e30 C. The mixture was stirredat 30 C for 3.5 h and quenched by using aqueous NaHCO3(saturated). The mixture was partitioned between CHCl3 and H2O.The organic layer was washed with aqueous NaHCO3 (saturated)and brine, dried (Na2SO4), and concentrated. The residue was purified by column chromatography (SiO2, 20% EtOAc in hexane) togive 17 (2.84 g, 5.33 mmol, 90%): 1H NMR (400 MHz, CDCl3) d 0.92(s, 9H), 3.10 (d, 1H, J 9.2), 3.52 (d, 1H, J 9.2), 4.55 (dd, 1H, J 6.0and 11.4), 4.65 (dd, J 4.6 and 11.4), 4.73 (dd, 1H, J 6.9 and 11.5),5.24 (s, 1H), 5.71 (d, 1H, J 5.0), 5.82 (dd, 1H, J 5.0 and 6.8),7.28e8.12 (m, 15H); 13C NMR (126 MHz, CDCl3) d 4.9, 4.8, 18.0,19.4, 19.4, 25.7, 28.3, 55.3, 64.4, 72.7, 74.9, 75.5, 82.7, 86.0, 107.5,113.1, 126.7, 127.8, 128.4, 130.2, 136.3, 145.0, 158.5. Anal. Calcd forC31H32O81/2H2O: C, 68.75; H, 6.14. Found: C, 68.66; H, 5.89.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 103,p. 460 - 472

77
[ 6974-32-9 ]
ethyl-4-oxo-6-(trifluoromethoxy)-1,4-dihydroquinoline-3-carboxylate [ No CAS ]
ethyl 6-(trifluoromethoxy)-1,4-dihydro-4-oxo-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)quinoline-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%		General procedure: Ethyl ester 6a or 7a (200 mg, 0.66 mmol) was added into a solution of BSTFA containing 1% of TMSCl (0.50 ml, 1.85 mmol) in anhydrous acetonitrile (3 ml) and the mixture was heated at 60 C under an Ar atmosphere for 3 h. To the resulting solution which was allowed to cool to room temperature, a solution of 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose 16 (334 mg, 0.66 mmol) in anhydrous acetonitrile (4 ml) was added followed by dropwise addition of TMSOTf (0.06 ml, 0.33 mmol). After 2 h of stirring, the reaction mixture was poured into ice-cold water (20 ml) and neutralized with a saturated aqueous solution of NaHCO3. The resulting solution was extracted with CHCl3 (3 × 20 ml) and the combinedS11organic layers were washed with water (3 × 20 ml), dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure to give products 17 and 18 as white crystals. Isolated nucleoside 17 was characterized and used in the next reactions without further purification. Nucleoside 18 was recrystallized from ethanol.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 5112 - 5115

78
[ 6974-32-9 ]
[ 93703-24-3 ]
8-bromo-3-methyl-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)purine-2,6-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%		A suspension of 8-bromo-3-methyl-3,7-dihydro-1H-purine-2,6-dione 4 (5.34 g,21.82 mmol) and a catalytic amount of (NH4)2SO4 (20 mg) in HMDS (25 mL) was heated to reflux (? 125 C) in an inert atmosphere under argon. A clear solution obtained after 30 min. Reflux continued for 3 h and cooled to room temperature. Excess HMDS was removed in vacuo to obtain white solid which is further dried at 90 C under vacuum for 2 h to remove traces of HMDS. Thus obtained white solid and 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (5a) (10.0 g, 19.83 mmol) were taken up in dry EtOAc (100 mL) under argon atmosphere. The reaction mixture is cooled to 0 C and SnCl4 (3.5 mL) was added drop wise in 15 min under argon atmosphere. After completion of the addition, reaction mixture was stirred for 15 min at 0 C before raised to room temperature. After 1 h stirring at room temperature, Na2CO3 (2.0 g), NaHCO3(2.0 g) were added to the reaction mixture. Reaction mixture was cooled to 5 C and purified water (25 mL) was added by maintaining the temperature at 5 C to 10 C. Reaction mixturewas filtered after 10 min and filtrate was washed with satd. NaHCO3, Na2CO3 and brine solution. Organic layer was dried over MgSO4 and distilled out in vacuo at 50 C to obtain white foam. Thus obtained product was dissolved in hot EtOAc (25mL) (50 C) and silica gel (15.0 g) (60-120 mesh), activated charcoal (2.0 g) was added. Stirred for 10 min at 50 C and filtered through the celite pad and washed the celite pad withhot EtOAc (100 mL). Distilled out the complete solvent to dryness to obtain crude 6a (11.6 g, 85 % yield) as white foam (Scheme-I). The crude product chromatographed (hexane-EtOAc, 6:4) to give the pure 6a (9.54 g, 70 % yield) as off white solid. m.p. >155 C; [alpha]D20= -33 (C = 1.0 in DCM), 1H NMR (400 MHz, CDCl3,) delta ppm 8.55 (s, 1H, N-H), 7.80-8.07 (m, 6H, o-Ar-H), 7.40-7.55 (m, 6H, p-Ar-H), 7.25-7.29 (m,3H, m-Ar-H), 6.30 (d, 1H, H-1?), 6.13 (m, 1H, H-2?), 4.95-5.01 (t, 2H, H-3? & 4?), 4.75 (t, 2H, -CH2), 3.55 (s, 3H, NCH3). 13C NMR (100 MHz, DMSO-d6, ppm) 165.1, 153.9, 151.2, 150.8, 135.0, 134.1, 133.0, 129.0, 128.2, 108.4, 90.2, 79.3, 30.1. MS (ES+) m/z: 687-689 (81Br). Anal. calcd. for C32H25BrN4O9: C, 55.74; H, 3.65; Br, 11.59; N, 8.13. Found: C, 55.81; H, 3.71; Br, 11.65; N, 8.15.

Reference： [1]Asian Journal of Chemistry,2016,vol. 28,p. 429 - 434

79
[ 6974-32-9 ]
[ 28888-44-0 ]
(2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(6,7-dimethoxy-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%		Step 1 Commercially available 6,7-dimethoxyquinazoline-2,4(1H,3H)-dione (220 mg, 0.991 mmol) and 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (500 mg, 0.991 mol) were dissolved in acetonitrile (5 mL), and N,O-bis(trimethylsilyl)acetamide (0.735 mL, 2.97 mmol) was added thereto, and the mixture was stirred at 60 C. for 20 minutes. After the reaction solution was cooled to room temperature, methanesulfonyl trimethylsilyl (0.627 mL, 3.47 mmol) was added thereto, and the mixture was stirred at 60 C. for 1 hour. After the reaction solution was cooled to room temperature, a saturated aqueous sodium bicarbonate solution was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over sodium sulfate. The residue obtained by evaporating the solvent under reduced pressure was purified by column chromatography (heptane/ethyl acetate) to obtain (2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(6,7-dimethoxy-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate (599 mg, yield: 91%).
91%		Step 1 Commercially available 6,7-dimethoxyquinazoline-2,4(1H,3H)-dione (220 mg, 0.991 mmol) and 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (500 mg, 0.991 mmol) were dissolved in acetonitrile (5 mL), and N,O-bis(trimethylsilyl)acetamide (0.735 mL, 2.97 mmol) was added thereto, and the mixture was stirred at 60 C. for 20 minutes. After the reaction solution was cooled to room temperature, methanesulfonyl trimethylsilyl (0.627 mL, 3.47 mmol) was added thereto, and the mixture was stirred at 60 C. for 1 hour. After the reaction solution was cooled to room temperature, a saturated aqueous sodium bicarbonate solution was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over sodium sulfate. The residue obtained by evaporating the solvent under reduced pressure was purified by column chromatography (heptane/ethyl acetate) to obtain (2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(6,7-dimethoxy-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate (599 mg, yield: 91%).

Reference： [1]Patent: US2015/376611,2015,A1 .Location in patent: Paragraph 0429
[2]Patent: US2017/354673,2017,A1 .Location in patent: Paragraph 0635; 0636

80
[ 6974-32-9 ]
[ 582313-57-3 ]
C₃₂H₂₅FN₄O₇ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 4518 - 4522

81
[ 6974-32-9 ]
[ 4212-49-1 ]
[ 25692-02-8 ]

Yield	Reaction Conditions	Operation in experiment
95%		Compound 105: To a solution of compound 104 (2.8 g, 20 mmol) in dry acetonitrile (30 mL) was added BSA (21 g, 100 mmol, 5 eq). The reaction mixture was stirred at 60 C for 4 h and cooled to room temperature. To this reaction mixture were added compound 103 (10.1 g, 20 mmol), TMSOTf (10.8 mL, 60 mmol, 3eq), and the resulted reaction mixture was stirred at 60 C for 4 h. Upon completion of the reaction as monitored by TLC, the reaction mixture was treated with methylene chloride and saturated sodium bicarbonate. The organic phase was separated, and the aqueous phase was extracted with dichloromethane. The combined organic phase was dried over anhydrous Na2SO4. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The crude product was purified by flash chromatography on a silica gel column giving 11 g desired compound 105 in 95% yield.

Reference： [1]Patent: EP2918275,2015,A1 .Location in patent: Paragraph 2126; 2127

82
[ 6974-32-9 ]
[ 6623-81-0 ]
C₃₁H₃₂N₂O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%		Compound 110: To a solution of compound 109 (1.42 g, 10 mmol) in dry acetonitrile (30 mL) was added BSA (10.5 g, 50 mmol). The reaction mixture was stirred at 60 C for 4 h and cooled to room temperature. To the reaction mixture were added compound 103 (5.04 g, 10 mmol) and TMSOTf (2.7 mL, 15 mmol). The resulted reaction mixture was stirred at 60 C for 4 h. Upon completion of the reaction as monitored by TLC, the reaction mixture was treated with methylene chloride and saturated sodium bicarbonate. The organic phase was separated, and the aqueous phase was extracted with methylene chloride. The combined organic phase was dried over anhydrous Na2SO4. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The crude product was purified by flash chromatography on a silica gel column giving 3.8 g desired compound 110 in 65% yield.

Reference： [1]Patent: EP2918275,2015,A1 .Location in patent: Paragraph 2131; 2132

83
[ 6974-32-9 ]
[ 163042-96-4 ]

Reference： [1]Patent: KR2015/10195,2015,A

84
[ 6974-32-9 ]
[ 78754-81-1 ]
C₃₄H₂₅ClN₂O₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		0.5 mmol of 5-chloro-2,4-quinazolinedione was added to 20 mL of anhydrous acetonitrile, N.2Under the protection, 1.0 mL (4 mmol) of NO-BSA was added dropwise and reacted at 25 C for 2 h.(0.55 mmol) of 1-acetoxy-2,3,5-tribenzoyloxy-1-beta-D-ribofuranose and 0.2 mL (1.1 mmol) of TMSOTf were simultaneously added to the above solution, 50-60 C, reaction 20-24 h.The solvent was removed by steaming and saturated with NaHCO3And saturated aqueous solution of NaCl.Silica gel spin drying, column chromatography separation purification products.The product was a pale yellow solid.

Reference： [1]Patent: CN106699824,2017,A .Location in patent: Paragraph 0030; 0031

85
[ 6974-32-9 ]
[ 149765-15-1 ]
[ 115479-42-0 ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 8589 - 8595

86
[ 6974-32-9 ]
[ 149765-15-1 ]
4-chloro-2-(N²-pivaloyl)amino-7-[(2,3,5-tri-O-benzoyl)-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 8589 - 8595

87
[ 6974-32-9 ]
[ 1000340-39-5 ]
3-bromo-4-chloro-N1-(2’,3’,5’-tri-O-benzoyl-β-D-ribofuranosyl)pyrrolo[2,3-b]pyridine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 8847 - 8865

88
[ 6974-32-9 ]
[ 115093-90-8 ]
[ 952429-08-2 ]

Reference： [1]European Journal of Medicinal Chemistry,2020,vol. 188

Same Skeleton Products

Related Products

Historical Records

Similar Product of
[ 6974-32-9 ]

A1669910[ 54447-56-2 ]

(2S,3R,4R,5R)-2-Acetoxy-5-((benzoyloxy)methyl-13C)tetrahydrofuran-3,4-diyl dibenzoate

Reason: Stable Isotope

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 6974-32-9 ] {[proInfo.proName]}

Quality Control of [ 6974-32-9 ]

Related Doc. of [ 6974-32-9 ]

Product Details of [ 6974-32-9 ]

Calculated chemistry of [ 6974-32-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 6974-32-9 ]

Application In Synthesis of [ 6974-32-9 ]

[ 6974-32-9 ] Synthesis Path-Upstream 1~12

[ 6974-32-9 ] Synthesis Path-Downstream 1~88

Similar Product of [ 6974-32-9 ]

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Similar Product of
[ 6974-32-9 ]