[ CAS No. 3690-10-6 ] {[proInfo.proName]}

Name: 3690-10-6|1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one|98%
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SKU: A162514
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2D 3D

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Quality Control of [ 3690-10-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 3690-10-6 ]

SDS Specification

Alternatived Products of [ 3690-10-6 ]

Product Details of [ 3690-10-6 ]

CAS No. :	3690-10-6	MDL No. :	MFCD04973699
Formula :	C₉H₁₂N₂O₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RPQZTTQVRYEKCR-WCTZXXKLSA-N
M.W :	228.20	Pubchem ID :	100016
Synonyms :	NSC309132;4-Deoxyuridine;Pyrimidin-2-one beta-ribofuranoside;Pyrimidin-2-one ribonucleoside

Calculated chemistry of [ 3690-10-6 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.56
Num. rotatable bonds :	2
Num. H-bond acceptors :	6.0
Num. H-bond donors :	3.0
Molar Refractivity :	51.44
TPSA :	104.81 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-8.79 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.51
Log Po/w (XLOGP3) :	-1.54
Log Po/w (WLOGP) :	-2.47
Log Po/w (MLOGP) :	-1.77
Log Po/w (SILICOS-IT) :	-1.54
Consensus Log Po/w :	-1.36

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.43
Solubility :	84.8 mg/ml ; 0.371 mol/l
Class :	Very soluble
Log S (Ali) :	-0.15
Solubility :	160.0 mg/ml ; 0.701 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	0.65
Solubility :	1020.0 mg/ml ; 4.48 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.72

Safety of [ 3690-10-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 3690-10-6 ]

* 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 [ 3690-10-6 ]
Downstream synthetic route of [ 3690-10-6 ]

[ 3690-10-6 ] Synthesis Path-Upstream 1~6

1
[ 3690-10-6 ]
[ 557-01-7 ]
[ 50-69-1 ]

Reference： [1] Journal of the American Chemical Society, 2009, vol. 131, # 44, p. 16088 - 16095
[2] Journal of the American Chemical Society, 2009, vol. 131, # 44, p. 16088 - 16095

2
[ 52523-24-7 ]
[ 3690-10-6 ]

Yield	Reaction Conditions	Operation in experiment
94%	With ammonia In methanol at 0 - 25℃;	To a cooled (0 °C) solution of the compound 15 (9.5 g, 17.6 mmol) in MeOH (100 mL) was added 7N NH₃ in MeOH (245 mL). The reaction mixture was stirred at 25 °C for 24 h and evaporated under reduced pressure. The residue was diluted with water and extracted with chloroform. The organic layer was dried over MgSO_4; filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (DCM : MeOH = 10 : 1) to give the compound 16 (3.8 g, 94percent) as a white solid. HNMR (400 MHz, methanol-d₄) δ 8.79 (dd, J = 6.8, 2.8 Hz, 1H), 8.57 (dd, J= 4, 2.8 Hz, 1H), 6.58 (dd, .7= 6.8, 4.4 Hz, 1H), 5.86 (s, 1H), 4.15-4.10 (m, 3H), 3.98 (dd, y= 12.4, 2.0 Hz, 1H), 3.79 (dd, J= 12.8, 2.0 Hz, 1H).

Reference： [1] Patent: WO2015/72784, 2015, A1, . Location in patent: Page/Page column 21; 22
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983, # 1, p. 127 - 130
[3] Tetrahedron Letters, 1994, vol. 35, # 10, p. 1597 - 1600
[4] Journal of Medicinal Chemistry, 1981, vol. 24, # 6, p. 662 - 666

3
[ 557-01-7 ]
[ 50-69-1 ]
[ 65025-04-9 ]
[ 3690-10-6 ]
[ 65025-05-0 ]

Reference： [1] Journal of the American Chemical Society, 2007, vol. 129, # 31, p. 9556 - 9557

4
[ 63500-40-3 ]
[ 3690-10-6 ]

Reference： [1] Journal of Organic Chemistry, 2011, vol. 76, # 15, p. 6075 - 6087

5
[ 6974-32-9 ]
[ 3690-10-6 ]

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

6
[ 13035-61-5 ]
[ 3690-10-6 ]

Reference： [1] Journal of Organic Chemistry, 2011, vol. 76, # 15, p. 6075 - 6087

[ 3690-10-6 ] Synthesis Path-Downstream 1~22

1
[ 67-64-1 ]
[ 3690-10-6 ]
[ 86030-38-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1983,p. 127 - 130
[2]Journal of Medicinal Chemistry,1981,vol. 24,p. 662 - 666

2
[ 40615-36-9 ]
[ 3690-10-6 ]
[ 170660-47-6 ]

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

3
[ 3690-10-6 ]
[ 99271-98-4 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1985,vol. 50,p. 393 - 417

4
[ 3690-10-6 ]
[ 2508-81-8 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 536 - 541
[2]Journal of Organic Chemistry,1992,vol. 57,p. 536 - 541

5
[ 52523-24-7 ]
[ 3690-10-6 ]

Yield	Reaction Conditions	Operation in experiment
94%	With ammonia; In methanol; at 0 - 25℃;	To a cooled (0 °C) solution of the compound 15 (9.5 g, 17.6 mmol) in MeOH (100 mL) was added 7N NH3 in MeOH (245 mL). The reaction mixture was stirred at 25 °C for 24 h and evaporated under reduced pressure. The residue was diluted with water and extracted with chloroform. The organic layer was dried over MgSO4; filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (DCM : MeOH = 10 : 1) to give the compound 16 (3.8 g, 94percent) as a white solid. HNMR (400 MHz, methanol-d4) delta 8.79 (dd, J = 6.8, 2.8 Hz, 1H), 8.57 (dd, J= 4, 2.8 Hz, 1H), 6.58 (dd, .7= 6.8, 4.4 Hz, 1H), 5.86 (s, 1H), 4.15-4.10 (m, 3H), 3.98 (dd, y= 12.4, 2.0 Hz, 1H), 3.79 (dd, J= 12.8, 2.0 Hz, 1H).

Reference： [1]Patent: WO2015/72784,2015,A1 .Location in patent: Page/Page column 21; 22
[2]Journal of the Chemical Society. Perkin transactions I,1983,p. 127 - 130
[3]Tetrahedron Letters,1994,vol. 35,p. 1597 - 1600
[4]Journal of Medicinal Chemistry,1981,vol. 24,p. 662 - 666

8
[ 557-01-7 ]
[ 50-69-1 ]
[ 65025-04-9 ]
[ 3690-10-6 ]
[ 65025-05-0 ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 9556 - 9557

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

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

10
[ 3690-10-6 ]
[ 170660-44-3 ]

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

11
[ 3690-10-6 ]
Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-(2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester [ No CAS ]

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

12
[ 3690-10-6 ]
[ 86030-40-2 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1983,p. 127 - 130
[2]Journal of the Chemical Society. Perkin transactions I,1983,p. 127 - 130

13
[ 3690-10-6 ]
[ 86030-39-9 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1983,p. 127 - 130

14
[ 3690-10-6 ]
[ 86030-41-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1983,p. 127 - 130

15
[ 3690-10-6 ]
[ 557-01-7 ]
[ 50-69-1 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 16088 - 16095
[2]Journal of the American Chemical Society,2009,vol. 131,p. 16088 - 16095

16
[ 53293-00-8 ]
[ 3690-10-6 ]
[ 1315330-25-6 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 6075 - 6087

17
[ 63500-40-3 ]
[ 3690-10-6 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 6075 - 6087

18
[ 13035-61-5 ]
[ 3690-10-6 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 6075 - 6087

19
[ 40615-36-9 ]
[ 3690-10-6 ]
1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(((3-methoxyphenyl)(4-methoxyphenyl)(phenyl)methoxy)methyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With pyridine; at 0 - 25℃;	To a cooled (0 °C) solution of the compound 16 (3.0 g, 13.2 mmol) in pyridine (33 mL) was added 4,4'-dimethoxytriphenylmethyl chloride (DMTCl) (5.6 g, 16.5 mmol) and the reaction mixture was stirred at 25 °C for 50 min. After evaporated under reduced pressure, the residue was purified by silica gel column chromatography (DCM : MeOH = 20 : 1) to give the compound 17 (4.4 g, 63percent) as a white solid. 1HNMR (400 MHz, CDC13) delta 8.63 (dd, J= 4.4, 3.2 Hz, 1H), 8.40 (dd, 7 = 5.6, 2.4 Hz, 1H), 7.63-7.16 (m, 9H), 6.84-6.81 (m, 4H), 6.14 (dd, J = 6.8, 4.0 Hz, 1H), 5.87 (d, J= 3.2 Hz, 1H), 4.43-4.39 (m, 3H), 3.80 (s, 6H), 3.51-3.41 (m, 2H).

Reference： [1]Patent: WO2015/72784,2015,A1 .Location in patent: Page/Page column 22

20
[ 40615-36-9 ]
[ 3690-10-6 ]
1-((2R,3R,4R,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3,4-bis((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one [ No CAS ]

Reference： [1]Patent: WO2015/72784,2015,A1

21
[ 97-72-3 ]
[ 3690-10-6 ]
(2R,3R,4R,5R)-2-((isobutyryloxy)methyl)-5-(2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl bis(2-methylpropanoate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With pyridine; dmap; at 25℃; for 15h;	Preparation of i2R3R,4R,5R)-2-((isobutwyloxy)methyr)-5-(2- oxopyrimidin- 1 (2H - yl tetrahydrofuran-3 ,4-diyl bis(2-methylpropanoate) (23) To a solution of the compound 16 (1.0 g, 4.4 mmol) in pyridine (12.5 mL) was added wo-butyric anhydride (12.5 mL) and DMAP (37.5 mg, 0.31 mmol) at 25 °C. The reaction mixture was stirred at same temperature for 15 h and evaporated under reduced pressure. The residue was dissolve in DCM and washed with an aqueous sodium bicarbonate. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Hexane : EtOAc = 1 : 1) to give the compound 23 (1.0 g, 52percent) as a white solid. 1HNMR (400 MHz, DMSO-d6) delta 8.59 (t, J = 3.4 Hz, 1H), 8.17 (dd, J = 6.4, 2.8 Hz, 1H), 6.52 (dd, J = 6.8, 4.0 Hz, 1H), 5.88 (d, J = 3.2 Hz, 1H), 5.48 (dd, / = 6.0, 3.6 Hz, 1H), 5.36 (t, J = 6.2 Hz, 1H), 4.38-4.24 (m, 3H), 2.58-2.51 (m, 3H), 1.06 (dd, J= 6.8, 3.2 Hz, 18H). MS (EI) for C21H30N2O8, found 439.1 (MH+).

Reference： [1]Patent: WO2015/72784,2015,A1 .Location in patent: Page/Page column 25; 26

22
[ 106-31-0 ]
[ 3690-10-6 ]
(2R,3R,4R,5R)-2-((butyryloxy)methyl)-5-(2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibutyrate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With pyridine; dmap; at 25℃; for 4h;	Preparation of (2R,3R,4R,5R)-2-((butyryloxy)methyl)-5-(2-oxopyrimidin- lQH)-yl)tetrahvdrofuran-3.4-diyl dibutyrate (22) To a solution of the compound 16 (1.0 g, 4.4 mmol) in pyridine (12.5 mL) was added butyric anhydride (12.5 mL) and DMAP (37.5 mg, 0.31 mmol) at 25 °C. The reaction mixture was stirred at same temperature for 4 h and evaporated under reduced pressure. The residue was dissolve in DCM and washed with an aqueous sodium bicarbonate. The organic layer was dried over MgSO4> filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Hexane : EtOAc = 1 : 1) to give the compound 22 (900 mg, 47percent) as a pale yellow oil. 'HNMR (400 MHz, CDC13) delta 8.62 (dd, J = 4.0, 2.8 Hz, 1H), 8.06 (dd, J = 6.8, 2.8 Hz, 1H), 6.39 (dd, J = 6.8, 4.4 Hz, 1H), 6.10 (d, J = 4.0 Hz, 1H), 5.42 (dd, J = 5.6, 4.0 Hz, 1H), 5.24 (t, J = 5.6 Hz, 1H), 4.43-4,37 (m, 3H), 2.37-2.30 (m, 6H), 1.69-1.59 (m, 6H), 0.95-0.91 (m, 9H). MS (EI) for C2]H30N2O8, found 439.2 (MH+).

Reference： [1]Patent: WO2015/72784,2015,A1 .Location in patent: Page/Page column 24; 25

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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. 3690-10-6 ] {[proInfo.proName]}

Quality Control of [ 3690-10-6 ]

Related Doc. of [ 3690-10-6 ]

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[ 3690-10-6 ] Synthesis Path-Upstream 1~6

[ 3690-10-6 ] Synthesis Path-Downstream 1~22

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