[ CAS No. 961-07-9 ] {[proInfo.proName]}

Name: 961-07-9|2-Amino-9-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3,9-dihydro-6H-purin-6-one|95%
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SKU: A530913
Price: 5.0 USD
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2D 3D

Structure of 961-07-9 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 961-07-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 961-07-9 ]

SDS Specification

Alternatived Products of [ 961-07-9 ]

Product Details of [ 961-07-9 ]

CAS No. :	961-07-9	MDL No. :	MFCD00080300
Formula :	C₁₀H₁₃N₅O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YKBGVTZYEHREMT-KVQBGUIXSA-N
M.W :	267.24	Pubchem ID :	135398592
Synonyms :	Deoxyguanosine;Guanine deoxyriboside;NSC 22837	Chemical Name :	2-Amino-9-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3,9-dihydro-6H-purin-6-one

Calculated chemistry of [ 961-07-9 ]

Physicochemical Properties

Num. heavy atoms :	19
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.5
Num. rotatable bonds :	2
Num. H-bond acceptors :	6.0
Num. H-bond donors :	4.0
Molar Refractivity :	64.34
TPSA :	139.28 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) :	-8.85 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.15
Log Po/w (XLOGP3) :	-1.3
Log Po/w (WLOGP) :	-1.97
Log Po/w (MLOGP) :	-1.18
Log Po/w (SILICOS-IT) :	-1.33
Consensus Log Po/w :	-1.13

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.9
Solubility :	33.9 mg/ml ; 0.127 mol/l
Class :	Very soluble
Log S (Ali) :	-1.13
Solubility :	19.9 mg/ml ; 0.0746 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.3
Solubility :	133.0 mg/ml ; 0.497 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.61

Safety of [ 961-07-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 961-07-9 ]

* 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 [ 961-07-9 ]
Downstream synthetic route of [ 961-07-9 ]

[ 961-07-9 ] Synthesis Path-Upstream 1~4

1
[ 961-07-9 ]
[ 51093-31-3 ]
[ 85888-50-2 ]
[ 85899-54-3 ]
[ 34371-14-7 ]

Reference： [1] Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1985, vol. 40, # 11, p. 1519 - 1531

2
[ 961-07-9 ]
[ 19916-78-0 ]
[ 73-40-5 ]
[ 34371-14-7 ]

Reference： [1] Journal of the Chemical Society. Perkin Transactions 2, 1998, # 6, p. 1365 - 1374

3
[ 961-07-9 ]
[ 4005-49-6 ]
[ 4546-72-9 ]

Reference： [1] Nucleosides, Nucleotides and Nucleic Acids, 2007, vol. 26, # 8-9, p. 905 - 909

4
[ 961-07-9 ]
[ 890-38-0 ]

Reference： [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 2, p. 305 - 312

[ 961-07-9 ] Synthesis Path-Downstream 1~88

1
[ 2181-42-2 ]
[ 961-07-9 ]
[ 578-76-7 ]
[ 107149-64-4 ]
[ 72398-32-4 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 2787 - 2792
[2]Journal of the Chemical Society. Perkin transactions I,1980,p. 2787 - 2792
[3]Journal of the Chemical Society. Perkin transactions I,1980,p. 2787 - 2792

2
[ 97-72-3 ]
[ 961-07-9 ]
[ 68892-42-2 ]

Yield	Reaction Conditions	Operation in experiment
75%		Example 1N -Isobutyryl-2 ' -deoxyguanosine (50)2'-Deoxyguanosine (49) (5 g, 18.72 mmol) was coevaporated with pyridine (100 niL) three times and suspended in dry pyridine (100 rnL). Trimethylchlorosilane (11.88 rnL, 93.63 mmol) was added, and the resulting solution was stirred at room temperature for 2 h. Isobutyric anhydride (15.54 mL, 93.65 mmol) was added, and the mixture was stirred at room temperature for 4 h under argon atmosphere. The reaction was cooled in an ice bath, and water (30 mL) was added. After 15 min, 29% aqueous ammonia (30 mL) was added, and the reaction was stirred for 15 min. The solution was then evaporated to near dryness, and the residue was dissolved in water (300 mL). The aqueous layer was washed with dichloromethane (150 mL) and crystallization occurred quickly in water. The compound was filtrated then dried overnight under vacuum to afford the title compound 50 (4.75 g, 75%) as a white solid. 1H NMR (DMSO-J6) delta 1.01-1.10 (m, 6H, 2xCH3), 2.20-2.26 (m, IH, H-2'), 2.46-2.57 (m, IH, H- ), 2.71-2.76 (m, IH, H- ), 3.43-3.55 (m, 2H, H-5', H-5"), 3.77- 3.81 (m, IH, H-4'), 4.31-4.35 (m, IH, H- ), 4.93 (br s, OH), 5.29 (br s, OH), 6.17 (t, IH, J = 6.0 Hz, H-I'), 8.20 (s, IH, H-8), 10.97 (br s, 2x NH).
75%		N2-Isobutyryl-2 '-deoxyguanosine (50)2'-Deoxyguanosine (49) (5 g, 18.72 mmol) was coevaporated with pyridine (100 mL) three times and suspended in dry pyridine (100 mL). Trimethylchlorosilane (11.88 mL, 93.63 mmol) was added, and the resulting solution was stirred at room temperature for 2 h. Isobutyric anhydride (15.54 mL, 93.65 mmol) was added, and the mixture was stirred at room temperature for 4 h under argon atmosphere. The reaction was cooled in an ice bath, and water (30 mL) was added. After 15 min, 29% aqueous ammonia (30 mL) was added, and the reaction was stirred for 15 min. The solution was then evaporated to near dryness, and the residue was dissolved in water (300 mL). The aqueous layer was washed with dichloromethane (150 mL) and crystallization occurred quickly in water. The compound was filtrated then dried overnight under vacuum to afford the title compound 50 (4.75 g, 75%) as a white solid. 1H NMR (DMSO-J6) delta 1.01-1.10 (m, 6H, 2xCH3), 2.20-2.26 (m, IH, H-2'), 2.46-2.57 (m, IH, H- ), 2.71-2.76 (m, IH, H- ), 3.43-3.55 (m, 2H, H-5 H-5"), 3.77-3.81 (m, IH, H-4'), 4.31-4.35 (m, IH, H- ), 4.93 (br s, OH), 5.29 (br s, OH), 6.17 (t, IH, J = 6.0 Hz, H-T), 8.20 (s, IH, H-8), 10.97 (br s, 2x NH).
		2'-deoxyguanosine hydrate (Gamma) was co-evaporated with pyridine and suspended in dry pyridine. Trimethyl silyl chloride was added and stirred for 30 minutes. Isobutyric anhydride was added and stirred for three hours. Water was added. The mixture was evaporated and dissolved in ethyl ether. After washing with water compound 2' precipitates.

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 1475 - 1481
[2]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 60 - 64
[3]Patent: WO2010/68708,2010,A2 .Location in patent: Page/Page column 44-45
[4]Patent: WO2008/143846,2008,A1 .Location in patent: Page/Page column 54-55
[5]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1996,vol. 35,p. 657 - 661
[6]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 7302 - 7309
[7]Synthesis,1983,p. 540 - 541
[8]Patent: WO2012/17434,2012,A2 .Location in patent: Page/Page column 33
[9]Organic and Biomolecular Chemistry,2012,vol. 10,p. 1510 - 1513

3
[ 961-07-9 ]
[ 4546-70-7 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; ammonium hydroxide; trifluoroacetic anhydride 1. ice bath, 10 min, 2. cooling, 1.5 h; Yield given. Multistep reaction;
	With chloro-trimethyl-silane; trimethylsilyl trifluoromethanesulfonate; ammonia; 1,1,1,3,3,3-hexamethyl-disilazane 1.) 10 h, 145 deg C; 2.) toluene, 48 h, 145 deg C; 3.) MeOH, H₂O, 4 h, reflux; Yield given. Multistep reaction;

Reference： [1]Fathi; Goswami; Kung; Gaffney; Jones [Tetrahedron Letters, 1990, vol. 31, # 3, p. 319 - 322]
[2]Seela; Gabler [Helvetica Chimica Acta, 1994, vol. 77, # 3, p. 622 - 630]

4
[ 961-07-9 ]
[ 142559-87-3 ]
[ 137608-88-9 ]
[ 88847-89-6 ]

Reference： [1]Journal de Chimie Physique et de Physico-Chimie Biologique,1991,vol. 88,p. 1053 - 1060

5
[ 961-07-9 ]
[ 142559-87-3 ]
[ 137608-88-9 ]
[ 88847-89-6 ]
[ 152785-98-3 ]

Reference： [1]Journal de Chimie Physique et de Physico-Chimie Biologique,1991,vol. 88,p. 1069 - 1076

6
[ 961-07-9 ]
[ 13389-03-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With N-Bromosuccinimide In water; acetonitrile at 20℃; for 1h;	Synthesis of 8-bromo-2’-deoxyguanosine, 8 The preparation of 8 was performed according to a published procedure with minor modifications.10 Asuspension of 2’-deoxyguanosine monohydrate 7 (320 mg, 1.1 mmol) in acetonitrile (12 mL) and water(3 mL) was treated with freshly crystallized N-bromosuccinimide (NBS) (from water) (300 mg, 1.7 mmol,1.5 equiv.) in three aliquots (~100 mg each) over 30 min, which converted to 10 min per addition. Thereaction mixture was stirred for an additional 30 min at room temperature. The reaction mixture wasfiltered through a celite pad. The residue was washed with cold acetone (2 x 3 mL) to yield off-white flakyprecipitates of compound 8. (385 mg, 1.1 mmol, quant.)
94%	With N-Bromosuccinimide In water for 0.25h; other guanosines; other brominating agent; var. solvents and time;
94%	With N-Bromosuccinimide In water for 0.25h;

94%	With N-Bromosuccinimide In water; acetonitrile at 20℃; for 0.75h;
91%	With N-Bromosuccinimide In water; acetonitrile at 20℃; for 0.5h;
91%	With N-Bromosuccinimide In water; acetonitrile at 20℃; for 1h;	2'-Deoxyguanosine (3) (2.00 g, 7.01 mmol, 1.00 eq) was suspended in a mixture of acetonitrile:water (80 mL:20 mL). N-Bromosuccinimide (2.00 g, 11.2 mmol, 1.60 eq) was added and the reaction mixture was stirred for 1 h at rt. The solvent was removed under reduced pressure and the residue suspended in acetone (25 mL). After filtration the crude product was washed with acetone (3 x 10 mL). The product (4) was obtained as a yellow solid in a yield of 91 % (2.21 g, 6.38 mmol).
87%	With N-Bromosuccinimide In water; acetonitrile at 20℃; for 1h;
85%	With N-Bromosuccinimide In water at 20℃; for 2h;
85%	With N-Bromosuccinimide In water; acetonitrile at 25℃; for 1h;
85%	With N-Bromosuccinimide at 20℃; for 2h;
80%	With N-Bromosuccinimide In water; acetonitrile at 20℃; for 0.5h;
78%	With N-Bromosuccinimide In water at 20℃; for 0.25h;
78%	With N-Bromosuccinimide In water; acetonitrile
78%	With N-Bromosuccinimide In water; acetonitrile at 20℃; for 1h;
74%	With bromine In water
74%	With N-Bromosuccinimide In water; acetonitrile at 0 - 20℃; for 0.5h;
69%	With N-Bromosuccinimide at 20℃; for 0.0833333h;
57%	With bromine In water
57%	With sodium azide; bromoisocyanuric acid monosodium salt In water; N,N-dimethyl-formamide at 20℃; for 0.5h;	General procedure: 5'-O-Monomethoxytrityl-N2-phenoxyacetylguanosine (33, 0.138 g, 0.2 mmol) was dissolved inaqueous DMF solution (H2O:DMF 1:4, 5 mL) under stirring. SMBI (1.1 equiv., 0.051 g, 0.22 mmol)was added at r.t. and the mixture stirred. Progress of the reaction was followed by TLC. An additionalamount of the reagent (0.15 equiv., 0.007 g) was added into the reaction mixture after 1.5 h. Oncompletion of the reaction by 2 h, the reaction mixture was filtered, evaporated to dryness underreduced pressure and coevaporated with water (2 × 2 mL). The crude reaction mixture was purified bycolumn chromatography (4%-5% MeOH in DCM, v/v) to afford nucleoside 34 (0.148 g, 96%) in pureform as a white solid.8-Bromo-5'-O-monomethoxytrityl-N2-phenoxyacetylguanosine (34).
	With bromine In water
	With N-Bromosuccinimide In water at 20℃; for 0.25h;
	With N-Bromosuccinimide In water at 20℃; for 0.25h;
	With N-Bromosuccinimide
	With N-Bromosuccinimide In water; acetonitrile
	With N-Bromosuccinimide In acetonitrile	1.1 2'-deoxyguanosine was brominated in acetonitrile by addition bromosuccinimide. The precipitated was filtered and used without further purification.
	With N-Bromosuccinimide In water; acetonitrile
	With N-Bromosuccinimide In acetonitrile
	With N-Bromosuccinimide In water; acetonitrile
	With N-Bromosuccinimide In water; acetonitrile at 20℃; for 0.5h; Inert atmosphere;

Reference： [1]Zheng, Yiying; Haratipour, Pouya; Kashemirov, Boris A.; McKenna, Charles E. [Tetrahedron Letters, 2021, vol. 67]
[2]Gannett; Sura [Synthetic Communications, 1993, vol. 23, # 11, p. 1611 - 1615]
[3]Gannett; Sura [Synthetic Communications, 1993, vol. 23, # 11, p. 1611 - 1615]
[4]Muenzel, Martin; Szeibert, Claudia; Glas, Andreas F.; Globisch, Daniel; Carell, Thomas [Journal of the American Chemical Society, 2011, vol. 133, # 14, p. 5186 - 5189]
[5]Dumas, Anaelle; Luedtke, Nathan W. [Journal of the American Chemical Society, 2010, vol. 132, # 51, p. 18004 - 18007]
[6]Holzberger, Bastian; Strohmeier, Julian; Siegmund, Vanessa; Diederichsen, Ulf; Marx, Andreas [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 9, p. 3136 - 3139]
[7]Garah, Mohamed El; Perone, Rosaria C.; Bonilla, Alejandro Santana; Haar, Sébastien; Campitiello, Marilena; Gutierrez, Rafael; Cuniberti, Gianaurelio; Masiero, Stefano; Ciesielski, Artur; Samorì, Paolo [Chemical Communications, 2015, vol. 51, # 58, p. 11677 - 11680]
[8]Amann, Nicole; Wagenknecht, Hans-Achim [Synlett, 2002, # 5, p. 687 - 691]
[9]Gubala, Vladimir; Betancourt, Jose E.; Rivera, Jose M. [Organic Letters, 2004, vol. 6, # 25, p. 4735 - 4738]
[10]Valis, Linda; Wagenknecht, Hans-Achim [Synlett, 2005, # 15, p. 2281 - 2284]
[11]Gillet, Ludovic C. J.; Schaerer, Orlando D. [Organic Letters, 2002, vol. 4, # 24, p. 4205 - 4208]
[12]Meier, Chris; Gräsl, Sonja [Synlett, 2002, # 5, p. 802 - 804]
[13]Location in patent: scheme or table Colis, Laureen C.; Chakraborti, Debasis; Hilario, Pablo; McCarty, Christopher; Basu, Ashis K. [Nucleosides, nucleotides and nucleic acids, 2009, vol. 28, # 2, p. 67 - 77]
[14]Romero-Pérez, Sonia; López-Martín, Isabel; Martos-Maldonado, Manuel C.; Somoza, Álvaro; González-Rodríguez, David [Organic Letters, 2020, vol. 22, # 1, p. 41 - 45]
[15]Kannan, Arunkumar; Burrows, Cynthia J. [Journal of Organic Chemistry, 2011, vol. 76, # 2, p. 720 - 723]
[16]Silerme, Stéphanie; Bobyk, Laure; Taverna-Porro, Marisa; Cuier, Camille; Saint-Pierre, Christine; Ravanat, Jean-Luc [Chemical Research in Toxicology, 2014, vol. 27, # 6, p. 1011 - 1018]
[17]Okamoto, Akimitsu; Ochi, Yuji; Saito, Isao [Chemical Communications, 2005, # 9, p. 1128 - 1130]
[18]Lin; Cheng; Ishiguro; Sartorelli [Journal of Medicinal Chemistry, 1985, vol. 28, # 9, p. 1194 - 1198]
[19]Maity, Jyotirmoy; Stromberg, Roger [Molecules, 2013, vol. 18, # 10, p. 12740 - 12750]
[20]Varaprasad, Chamakura V.; Bulychev, Nickolai; Grollman, Arthur P.; Johnson, Francis [Tetrahedron Letters, 1996, vol. 37, # 1, p. 9 - 12]
[21]Meier; Graesl; Detmer; Marx [Nucleosides, nucleotides and nucleic acids, 2005, vol. 24, # 5-7, p. 691 - 694]
[22]Boege; Szombati; Meier [Nucleosides, nucleotides and nucleic acids, 2007, vol. 26, # 6-7, p. 705 - 708]
[23]Location in patent: scheme or table Lena, Stefano; Neviani, Paolo; Masiero, Stefano; Pieraccini, Silvia; Spada, Gian Piero [Angewandte Chemie - International Edition, 2010, vol. 49, # 21, p. 3657 - 3660]
[24]Location in patent: experimental part Schlitt, Katherine M.; Millen, Andrea L.; Wetmore, Stacey D.; Manderville, Richard A. [Organic and Biomolecular Chemistry, 2011, vol. 9, # 5, p. 1565 - 1571] Location in patent: experimental part Omumi, Alireza; Millen, Andrea L.; Wetmore, Stacey D.; Manderville, Richard A. [Chemical Research in Toxicology, 2011, vol. 24, # 10, p. 1694 - 1709]
[25]Current Patent Assignee: HEBREW UNIVERSITY OF JERUSALEM; Yissum Research & Development (in: Hebrew University) - WO2012/17434, 2012, A2 Location in patent: Page/Page column 36
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7
[ 68743-68-0 ]
[ 961-07-9 ]
[ 59578-62-0 ]
[ 100021-45-2 ]
3-hydroxy-1-(3-pyridyl)-1-butanone [ No CAS ]
[ 100044-90-4 ]

Reference： [1]Journal of the American Chemical Society,1986,vol. 108,p. 1292 - 1295
[2]Journal of the American Chemical Society,1986,vol. 108,p. 1292 - 1295

8
[ 68743-68-0 ]
[ 961-07-9 ]
[ 100021-45-2 ]
[ 100044-90-4 ]
[ 100021-47-4 ]
2'-deoxy-N-<1-methyl-3-oxo-3-(3-pyridyl)-propyl>guanosine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1986,vol. 108,p. 1292 - 1295

9
[ 10504-60-6 ]
[ 961-07-9 ]
[ 76567-63-0 ]
[ 5132-79-6 ]

Reference： [1]Bulletin de la Societe Chimique de France,1984,vol. 2,p. 431 - 434

10
[ 68892-42-2 ]
[ 961-07-9 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1994,p. 1833 - 1838

11
[ 4331-29-7 ]
[ 961-07-9 ]
[ 127553-27-9 ]

Reference： [1]Nucleosides and Nucleotides,1995,vol. 14,p. 477 - 480

12
[ 6478-73-5 ]
[ 961-07-9 ]
[ 4600-73-1 ]

Reference： [1]Nucleosides and Nucleotides,1995,vol. 14,p. 477 - 480

13
[ 961-07-9 ]
[ 78581-99-4 ]
(2R,3S,5R)-5-(5,6-Difluoro-benzoimidazol-1-yl)-2-hydroxymethyl-tetrahydro-furan-3-ol [ No CAS ]

Reference： [1]Nucleosides and Nucleotides,1995,vol. 14,p. 477 - 480

14
[ 405-39-0 ]
[ 961-07-9 ]
(S)-2,6-Bis-benzyloxycarbonylamino-hexanoic acid (2R,3S,5R)-5-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester [ No CAS ]
[ 173410-91-8 ]

Reference： [1]Journal of the American Chemical Society,1995,vol. 117,p. 12408 - 12415

15
[ 684-93-5 ]
[ 961-07-9 ]
[ 964-21-6 ]
[ 5132-79-6 ]
[ 812-00-0 ]
[ 813-78-5 ]
[ 578-76-7 ]
[ 28074-91-1 ]

Reference： [1]Tetrahedron,1997,vol. 53,p. 4063 - 4082

16
[ 961-07-9 ]
[ 63521-92-6 ]
[ 173346-59-3 ]

Reference： [1]Tetrahedron,1997,vol. 53,p. 2731 - 2750

17
[ 961-07-9 ]
[ 137608-88-9 ]
[ 88847-89-6 ]
N-[(1R,9R,10S)-10-Hydroxy-4-oxo-7,12-dioxa-2,5-diaza-tricyclo[7.2.1.0^2,6]dodec-(3E)-ylidene]-guanidine [ No CAS ]
[ 137608-89-0 ]
[ 137608-90-3 ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 719 - 723

18
[ 4546-70-7 ]
[ 961-07-9 ]

Yield	Reaction Conditions	Operation in experiment
91%	With adenosine aminohydrolase (EC 3.5.4.4) In dimethyl sulfoxide Ambient temperature; aq. sodium phosphate buffer (pH 7.4);

Reference： [1]Robins, Morris J.; Zou, Ruiming; Hansske, Fritz; Wnuk, Stanislaw F. [Canadian Journal of Chemistry, 1997, vol. 75, # 6, p. 762 - 767]

19
[ 961-07-9 ]
[ 137608-88-9 ]
[ 88847-89-6 ]
[ 152785-98-3 ]

Reference： [1]Photochemistry and Photobiology,1996,vol. 63,p. 768 - 778

20
[ 961-07-9 ]
[ 88847-89-6 ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 11373 - 11380
[2]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2141 - 2144
[3]Photochemistry and Photobiology,2000,vol. 72,p. 619 - 624
[4]Chemical Research in Toxicology,1999,vol. 12,p. 270 - 277
[5]Chemical Research in Toxicology,2002,vol. 15,p. 426 - 432
[6]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3627 - 3631
[7]Journal of Organic Chemistry,2011,vol. 76,p. 720 - 723

21
[ 961-07-9 ]
[ 137608-88-9 ]
[ 88847-89-6 ]
[ 152785-98-3 ]
N-[(1R,9R,10S)-10-Hydroxy-4-oxo-7,12-dioxa-2,5-diaza-tricyclo[7.2.1.0^2,6]dodec-(3E)-ylidene]-guanidine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1998,vol. 120,p. 3549 - 3559

22
[ 961-07-9 ]
[ 137608-88-9 ]
[ 88847-89-6 ]
[ 137608-89-0 ]
[ 137608-90-3 ]

Reference： [1]Chemical Research in Toxicology,1995,vol. 8,p. 379 - 388
[2]Chemical Research in Toxicology,1995,vol. 8,p. 379 - 388
[3]Chemical Research in Toxicology,1995,vol. 8,p. 379 - 388

23
[ 961-07-9 ]
[ 88847-89-6 ]
[ 137608-89-0 ]
[ 137608-90-3 ]

Reference： [1]Chemical Research in Toxicology,1995,vol. 8,p. 379 - 388

24
[ 50-32-8 ]
[ 961-07-9 ]
[ 39000-82-3 ]
[ 114378-32-4 ]

Reference： [1]Chemical Research in Toxicology,1998,vol. 11,p. 1201 - 1208

25
[ 50-32-8 ]
[ 961-07-9 ]
[ 39000-82-3 ]
7-(benzo[a]pyren-6-yl)adenine [ No CAS ]

Reference： [1]Chemical Research in Toxicology,1998,vol. 11,p. 1201 - 1208

26
[ 961-07-9 ]
[ 73-40-5 ]
[ 137608-88-9 ]
[ 88847-89-6 ]
2-amino-4-oxo-5-formamido-6-<N-(2'-deoxy-β-D-ribofuranosyl)>pyrimidine [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),1999,p. 1875 - 1880

27
[ 961-07-9 ]
[ 88847-89-6 ]
[ 152785-98-3 ]

Reference： [1]Photochemistry and Photobiology,2000,vol. 71,p. 12 - 19

28
[ 961-07-9 ]
6,7-Dimethoxycoumarin radical cation [ No CAS ]
[ 120-08-1 ]
2'-deoxyguanosine radical cation [ No CAS ]

Reference： [1]Photochemistry and Photobiology,2000,vol. 72,p. 155 - 162

29
[ 700-06-1 ]
[ 961-07-9 ]
9-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-[(1H-indol-3-ylmethyl)-amino]-1,9-dihydro-purin-6-one [ No CAS ]

Reference： [1]Chemical Research in Toxicology,2001,vol. 14,p. 1014 - 1024

30
[ 25152-84-5 ]
[ 961-07-9 ]
[ 288863-37-6 ]
1-[3-(2'-deoxy-β-D-erythro-pentafuranosyl)-5,9-dihydro-9H-imidazo[2,1-i]purin-9-hydroxy]-7-yl}-2-one-3-octanol [ No CAS ]

Reference： [1]Chemical Research in Toxicology,2000,vol. 13,p. 601 - 609

31
[ 544-35-4 ]
[ 961-07-9 ]
[ 62962-42-9 ]
[ 108929-11-9 ]
[ 56287-13-9 ]

Yield	Reaction Conditions	Operation in experiment
	With tert.-butylhydroperoxide In methanol at 50℃; for 72h;

Reference： [1]Ham, Amy-Joan L.; Ranasinghe, Asoka; Koc, Hasan; Swenberg, James A. [Chemical Research in Toxicology, 2000, vol. 13, # 12, p. 1243 - 1250]

32
[ 961-07-9 ]
[ 88847-89-6 ]
[ 168701-80-2 ]
8-nitro-2'-deoxyguanosine [ No CAS ]

Reference： [1]Chemical Research in Toxicology,2001,vol. 14,p. 438 - 450

33
[ 89-87-2 ]
[ 961-07-9 ]
N-(2'-deoxyguanosin-8-yl)-2,4-dimethylaniline [ No CAS ]
6-(2'-deoxyguanosin-N₁-yl)-2,4-dimethylaniline [ No CAS ]

Reference： [1]Chemical Research in Toxicology,1999,vol. 12,p. 1223 - 1233

34
[ 194-59-2 ]
[ 961-07-9 ]
2-amino-7-(7H-dibenzo[c,g]carbazol-5-yl)-1,7-dihydro-purin-6-one [ No CAS ]
2-amino-7-(7H-dibenzo[c,g]carbazol-6-yl)-1,7-dihydro-purin-6-one [ No CAS ]
2-amino-8-(7H-dibenzo[c,g]carbazol-6-yl)-1,7-dihydro-purin-6-one [ No CAS ]

Reference： [1]Chemical Research in Toxicology,1997,vol. 10,p. 225 - 233

35
[ 961-07-9 ]
[ 88847-89-6 ]
spiroiminodihydantoin deoxiribonucleoside [ No CAS ]

Reference： [1]Organic Letters,2002,vol. 4,p. 537 - 540
[2]Organic Letters,2002,vol. 4,p. 537 - 540
[3]Journal of Mass Spectrometry,2007,vol. 42,p. 1326 - 1332

36
[ 961-07-9 ]
[ 73-40-5 ]
[ 88847-89-6 ]

Reference： [1]Journal of Physical Chemistry B,2002,vol. 106,p. 7704 - 7712

37
[ 4291-63-8 ]
[ 961-07-9 ]
[ 106449-56-3 ]

Reference： [1]Pharmazie,2003,vol. 58,p. 122 - 124

38
[ 961-07-9 ]
[ 1839-18-5 ]
[ 4291-63-8 ]

Reference： [1]Helvetica Chimica Acta,2002,vol. 85,p. 1901 - 1908
[2]ChemCatChem,2018,vol. 10,p. 4406 - 4416

39
[ 4546-70-7 ]
[ 961-07-9 ]

Yield	Reaction Conditions	Operation in experiment
93.8%	With sodium hydroxide; tris(hydroxymethyl)methylamine hydrochloride In water monomer at 40℃; for 13h; Enzymatic reaction;	4.2 (2) Synthesis of 2'-deoxyguanosine To the reaction mixture (1 mL) obtained in (1) above, 20% sodium hydroxide (10 μL), 1 mol/L Tris-HCl buffer (pH 7.0) (0.1 mL), and adenosine deaminase (50 units/mL) were sequentially added, and the mixture was incubated at 40° C. for 13 hours with stirring. As a result, 2'-deoxyguanosine (41.2 mmol/L) was synthesized from 2,6-diaminopurine-2'-deoxyriboside (43.9 mmol/L) (mole yield: 93.8%).
84%	With adenosine deaminase In aq. phosphate buffer; dimethyl sulfoxide at 20℃; for 24h; Enzymatic reaction;	4.10. 2′-Deoxygunosine (2) ADA (1 g, 2.7 units/mg protein) was added to a solution of 3 (2.65 g,100 mmol) in DMSO (200 mL) and aqueous sodium phosphate buffer(0.1 mol/L, 2.5 L, pH = 7.4) and the mixture was stirred at room temperaturefor 24 h. Volatiles were evaporated in vacuo and the residue wasapplied to a column of Dowex 1 × 2 (OH-), which was washed sequentiallywith H2O, 80% MeOH-H2O and H2O. The product was then eluted(30 mmol/L aqueous Et3NH·HCO3) and fractions were evaporated severaltimes with H2O, and recrystallized from H2O to give 2 as a white solid(22 g, 84% yield).White solid. mp 252-254 °C (decomposition, lit.[23] 250-252 °C). 1HNMR (400 MHz, DMSO-d6) 10.78 (s, 1H, NH), 7.77 (s, 1H, 8-H), 6.53(s, 2H, NH2), 6.01 (d, J = 4.4 Hz, 1H, 1′-H), 5.69 (d, J = 4.8 Hz, 1H, 4′-H),5.59 (d, J = 2.0 Hz, 1H, OH), 4.04 (t, J = 4.0 Hz, 1H, 3′-H), 3.74 (d, J = 4.4 Hz,1H, 5′-H), 2.78-2.72 (m, 1H, 2′-H), 2.32-2.27 (m, 1H, 2′-H); 13C NMR(100 MHz, DMSO-d6) 156.9 (6-C), 156.6 (2-C), 151.0 (4-C), 136.9 (8-C),115.6 (5-C), 84.1 (1′-C), 83.3 (4′-C), 75.4 (3′-C), 60.9 (5′-C), 37.1 (2′-C);HRMS calcd for C10H14N5O4 [M + H]+ 268.1040, found 268.1040.
	With sodium hydroxide; Tris-HCl buffer; E_. coli adenosine deaminase In water monomer at 40℃; for 13h; Enzymatic reaction;

Reference： [1]Current Patent Assignee: YAMASA CORPORATION - US2005/170470, 2005, A1 Location in patent: Page/Page column 7
[2]Xia, Ran; Chen, Lei-Shan; Xu, Shao-Hong; Xia, Chao; Sun, Li-Ping [Nucleosides, nucleotides and nucleic acids, 2022, vol. 41, # 7, p. 593 - 604]
[3]Okuyama, Kiyoshi; Shibuya, Susumu; Hamamoto, Tomoki; Noguchi, Toshitada [Bioscience, Biotechnology and Biochemistry, 2003, vol. 67, # 5, p. 989 - 995]

40
[ 961-07-9 ]
[ 88847-89-6 ]
[ 142559-87-3 ]
spiroiminodihydantoin deoxiribonucleoside [ No CAS ]
[ 444816-83-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 2157 - 2162

41
[ 951-78-0 ]
[ 73-40-5 ]
[ 66-22-8 ]
[ 961-07-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium dihydrogenphosphate; multimeric uridine phosphorylase-Sepabeads-PEI-DX; purine nucleoside phosphorylase-glyoxyl-agarose In water at 45℃; for 24h;

Reference： [1]Ubiali, Daniela; Rocchietti, Silvia; Scaramozzino, Francesca; Terreni, Marco; Albertini, Alessandra M.; Fernandez-Lafuente, Roberto; Guisan, Jose Manuel; Pregnolato, Massimo [Advanced Synthesis and Catalysis, 2004, vol. 346, # 11, p. 1361 - 1366]

42
[ 961-07-9 ]
dehydro-guanidinohydantoin [ No CAS ]
[ 88847-89-6 ]
(5'R)-5',8-cyclo-2'-deoxyguanosine [ No CAS ]
N¹-(β-D-erythro-pentofuranosyl)-5-guanidinohydantoin [ No CAS ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2006,vol. 25,p. 259 - 278

43
[ 961-07-9 ]
[ 88847-89-6 ]
[ 152785-98-3 ]
spiroiminodihydantoin deoxiribonucleoside [ No CAS ]

Reference： [1]Tetrahedron,2006,vol. 62,p. 10709 - 10715

44
[ 961-07-9 ]
[ 235439-61-9 ]
[ 142559-87-3 ]
[ 137608-88-9 ]
[ 88847-89-6 ]

Reference： [1]Photochemistry and Photobiology,2006,vol. 82,p. 191 - 199

45
[ 961-07-9 ]
[ 68892-42-2 ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2002,vol. 21,p. 393 - 400
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1993,vol. 32,p. 916 - 919
[3]Helvetica Chimica Acta,1982,vol. 65,p. 2372 - 2393
[4]Journal of the American Chemical Society,1982,vol. 104,p. 1316 - 1319
[5]Synthesis,1984,p. 965 - 968

46
[ 21740-23-8 ]
[ 961-07-9 ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2001,vol. 20,p. 1291 - 1293

47
[ 961-07-9 ]
[ 68892-41-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: pyridine / 0.5 h / 0 °C 2: pyridine / 2 h 3: aq. NH₄OH / pyridine / 0.5 h 4: 72 percent / DMAP, TEA / pyridine / 1 h
	Multi-step reaction with 3 steps 1: pyridine; methanol / 5 h / 20 °C 2: NaOH / ethanol; H₂O / 0.67 h / 0 - 3 °C 3: 84 percent / 1.) pyridine, 0 deg C, 16 h, 2.) pyridine, CH₃OH, 20 deg C, 1 h
	Multi-step reaction with 2 steps 1: 1.) 1,1,1,3,3,3-hexamethyldisilazane / 1.) DMF, 5 h, 2.) pyridine, 16 h 2: 87 percent / 4-dimethylaminopyridine / pyridine; dioxane / 2 h

	Multi-step reaction with 3 steps 1: 90 percent / pyridine / CHCl₃ / 2 h / Ambient temperature 2: 77 percent / aq. NaOH / ethanol / 0.25 h / 0 °C 3: 85 percent / pyridine / 2 h / Ambient temperature
	Multi-step reaction with 2 steps 1.1: pyridine; chloro-trimethyl-silane / 0.5 h / Cooling with ice 1.2: 2 h / 20 °C 2.1: pyridine; dmap; triethylamine / 4 h / 20 °C
	Multi-step reaction with 2 steps 1.1: pyridine; chloro-trimethyl-silane / 0.5 h / Cooling with ice bath 1.2: 2.5 h / 20 °C 1.3: 0.5 h / Cooling with ice 2.1: pyridine / 5 h / 20 °C

Reference： [1]Awasthi, S. K.; Khanna, V.; Watal, G.; Misra, K. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 9, p. 916 - 919]
[2]Denny, William A.; Leupin, Werner; Kearns, David R. [Helvetica Chimica Acta, 1982, vol. 65, # 8, p. 2372 - 2393]
[3]McGee, Danny P. C.; Martin, John C.; Webb, Austin S. [Synthesis, 1983, # 7, p. 540 - 541]
[4]Charubala, R.; Uhlmann, E.; Beiter, A. H.; Pfleiderer, W. [Synthesis, 1984, # 11, p. 965 - 968]
[5]Janczyk, Matthaeus; Appel, Bettina; Springstubbe, Danilo; Fritz, Hans-Joachim; Mueller, Sabine [Organic and Biomolecular Chemistry, 2012, vol. 10, # 8, p. 1510 - 1513]
[6]Current Patent Assignee: HEBREW UNIVERSITY OF JERUSALEM; Yissum Research & Development (in: Hebrew University) - US2011/86813, 2011, A1

48
[ 554-68-7 ]
[ 961-07-9 ]
[ 93635-99-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate; In methanol; hexane; N,N-dimethyl-formamide;	Step (1b) N-isobutyryl <strong>[961-07-9]deoxyguanosine</strong> A chilled 25% methanolic solution of sodium methoxide (76 g, 0.35 mol. 0.5 eq based on dG) is added slowly to a cooled mixture (about -18 to about -20 C.) of the dehydrated organic phase from step (1a) above diluted in 2.0 l of methanol. The temperature of the mixture is maintained at or below -15 C. during the addition, and during the course of the de-protection reaction. Samples are taken about every 30 min. Additional NaOCH3 is used to keep the reaction going and to lower the combined di- and triacylated dG level to below 3%. When the reaction is completed, 100 g of triethylammonium chloride (0.7 mol, 1 eq based on dG) is added to the mixture, which is stirred for 30 min at -15 C. and warmed up to 20 C. and stirred for an additional hour (at 20 C.). 2.0 l of DMF is added to the mixture, which is distilled at ambient pressure at about 80 C. to remove methanol, methylene chloride, methyl isobutyrate, triethylamine and other low-boiling components. When no more distillate is collected, 2.0 l of hexane is added to the mixture, which is distilled again to azeotropically remove any residual methanol.

Reference： [1]Patent: US2003/162957,2003,A1

49
magnesium hydroxide [ No CAS ]
2,3-dideoxy-α-D-ribose-1-phosphate [ No CAS ]
2-deoxyribose-1-phosphate di(monocyclohexylammonium) salt [ No CAS ]
[ 73-40-5 ]
[ 961-07-9 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium hydroxide; In water;	Example 49 Preparation of 2'-deoxyguanosine To 20 g of purified water were added 3.22 g of 2-deoxyribose-1-phosphate di(monocyclohexylammonium) salt prepared in Example 24 (7.72 mmol), 1.11 g of guanine (7.34 mmol) and 0.67 g of magnesium hydroxide (11.48 mmol). The reaction mixture was adjusted to pH 9 with a 20% aqueous solution of sodium hydroxide. To the mixture was added 0.1 mL of the above enzyme solution (0.1 mL), and the mixture was reacted with stirring at 50 C. for 8 hours. HPLC analysis for the reaction mixture after 8 hours indicated that the desired 2'-deoxyguanosine was provided with a reaction yield of 99%.

Reference： [1]Patent: US2002/193314,2002,A1

50
tris(trimethyl)silyltriflate [ No CAS ]
[ 961-07-9 ]
2-Amino-(2-deoxy-β-D-erythropentofuranosyl)adenine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24.2%	With chloro-trimethyl-silane; ammonia; 1,1,1,3,3,3-hexamethyl-disilazane; In methanol; water; toluene;	EXAMPLE 32 2-Amino- (2-deoxy-beta-D-erythropentofuranosyl)adenine 5.0 g (18.6 mmol) <strong>[961-07-9]deoxyguanosine</strong> is silylated for 10 hours at 145 C. with 200 ml hexamethyldisilazane (HMDS) and 0.5 ml trimethylchlorosilane (TCS) in the same manner as the corresponding ribo compound [2][3]. Subsequently excess HMDS is removed by distillation under normal pressure. The remaining turbid syrup ([2]) is taken up in a mixture of 30 ml absolute toluene and 2 ml HMDS. This mixture is transferred into a 300 ml autoclave. After addition of 4 ml of a 0.5 M solution (2 mmol) of tris(trimethyl)silyltriflate in absolute toluene, it is pressurized for 0.5 hours with NH3 (5 bar) at 0 C.; then it is heated for 48 hours at 145 C. (external temperature regulation). After cooling to room temperature, the NH3 is carefully vented. The solid residue is suspended in 150 ml methanol (ultrasonic bath), admixed with 150 ml water and transsilylated for 4 hours at 100 C. After removing the methanol by distillation, 250 ml water is added, the solution is admixed with active charcoal, hot-filtered and rewashed with 100 ml hot water. The yellow filtrate is applied to a Dowex 12 column (202 cm, OH-). Elution with 500 ml water yields a main zone from which the product (1.2 g, 24.2%) is obtained after evaporation as a yellow powder. The product is identical with an authentic sample [1][4-6). TLC (silica gel, CH2 Cl2 /MeOH 4:1): Rf =0.4. UV (MeOH):=lambdamax 217 (23500), 256 (8900), 282 (9900). 13 C-NMR in ((D6)DMSO): 160.2 C(6); 156.3 C(2); 151.3 C(4); 135.9 C(8); 113.5 C(5); 87.8 C(4'); 83.2 C(1'); 71.1 C(3'); 62.1 C(5').

Reference： [1]Patent: US6147199,2000,A

51
bromine-water [ No CAS ]
[ 961-07-9 ]
[ 13389-03-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate In water	I.I I. To a cooled (0° C.) solution of 2'-deoxyguanosine (5.0 g, available from Sigma Chemical Company) in 25 mL of water, a saturated solution of bromine-water is added dropwise until the suspension becomes opaque and a yellow color persists. The precipitated 8-bromodeoxyguanosine is removed by filtration and washed with cold water followed by acetone. The solid is then recrystallized from methanol-water containing sodium bicarbonate to yield 8-bromodeoxyguanosine.

Reference： [1]Current Patent Assignee: UNIVERSITY OF WASHINGTON - US6132776, 2000, A

52
[ 961-07-9 ]
[ 2719-27-9 ]
[ 168466-00-0 ]

Yield	Reaction Conditions	Operation in experiment
	With chloro-trimethyl-silane; ammonium fluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; methanol; ice-water; ethanol; water; toluene;	EXAMPLE A1 Preparation of N2 -cyclohexylcarbonyl-<strong>[961-07-9]2'-<strong>[961-07-9]deoxyguanosine</strong></strong> 28 g of <strong>[961-07-9]deoxyguanosine</strong> are taken up in 3200 ml of absolute pyridine and the solution is then concentrated to dryness under vacuum at 50 C. The nucleoside is taken up with 340 ml of diisopropylethylamine and to the solution are added 127 ml of trimethylchlorosilane. The mixture is stirred for 2 hours at room temperature and then a solution of 100 ml of absolute tetrahydrofuran (THF) and 20.4 ml of cyclohexanecarbonyl chloride is added over 1 hour. The reaction mixture is cooled to 0 C. after 16 hours and 100 ml of methanol are added over 1 hour, followed by the addition of 180 ml of an aqueous 35% solution of ammonium fluoride. One hour after addition of the fluoride, the volatile constituents are removed by evaporation under vacuum at 50 C. Residual pyridine is removed by coevaporation with 2200 ml of toluene. The crude product is stirred with 700 ml of ice-water for 30 minutes and then filtered. The filter cake is treated in 700 ml of a boiling solution of ethanol/water (7:3 v/v). Insoluble matter is filtered off hot. The title compound precipitates from the cooled filtrate and is vacuum dried. 1 H-NMR:(DMSO) 8.14: s, H8; 6.21: t, 1'; 5.34, 4.97: 2H s (broad) OH; 4.88: m, 3'; 3.8: m, 4'; 2.5: 2H: 2'-, H1 of CC group; 2.26: m, 2'; 1.1-1.9: 10H, m, CC group.

Reference： [1]Patent: US5639867,1997,A

53
[ 19962-37-9 ]
[ 961-07-9 ]
[ 1061382-93-1 ]
[ 4318-06-3 ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2007,vol. 26,p. 905 - 909

54
[ 961-07-9 ]
[ 4005-49-6 ]
[ 4546-72-9 ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2007,vol. 26,p. 905 - 909

55
[ 961-07-9 ]
[ 79-30-1 ]
[ 68892-42-2 ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2008,vol. 27,p. 1282 - 1300

56
[ 961-07-9 ]
[ 22161-81-5 ]
[ 1069110-41-3 ]

Reference： [1]Organic Letters,2008,vol. 10,p. 4409 - 4412

57
calf thymus DNA, γ-irradiated [ No CAS ]
[ 31077-24-4 ]
[ 105929-27-9 ]
[ 961-07-9 ]
[ 88847-89-6 ]
[ 117182-88-4 ]
(5'R)-5',8-cyclo-2'-deoxyadenosine [ No CAS ]
(5'R)-5',8-cyclo-2'-deoxyguanosine [ No CAS ]
[ 951-77-9 ]
[ 50-89-5 ]
[ 958-09-8 ]

Reference： [1]Organic and Biomolecular Chemistry,2010,vol. 8,p. 3211 - 3219

58
[ 141-76-4 ]
[ 961-07-9 ]
3-(N₇-guaninyl)propionic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ISOPROPYLAMIDE at 20 - 100℃;

Reference： [1]Location in patent: experimental part Cheng, Guang; Wang, Mingyao; Villalta, Peter W.; Hecht, Stephen S. [Chemical Research in Toxicology, 2010, vol. 23, # 6, p. 1089 - 1096]

59
5'-d(AGTAT[5-ethynyl-U]GACCTA)-3' [ No CAS ]
[ 959326-89-7 ]
[ 961-07-9 ]
[ 61135-33-9 ]
[ 50-89-5 ]
[ 958-09-8 ]

Reference： [1]Chemistry - A European Journal,2010,vol. 16,p. 14385 - 14396

60
[ 1468-39-9 ]
[ 961-07-9 ]
[ 68892-42-2 ]

Yield	Reaction Conditions	Operation in experiment
82%		Step 1-N2-Isobutyryl-2'-deoxyguanosine (B5-I)2'-Deoxyguanosine (5.705 g, 20 mmol) was co-evaporated with anhydrous pyridine and then suspended in 200 mL anhydrous pyridine. Trimethylchlorosilane (13 mL, 100 mmol) was added slowly to the suspension cooled in an ice-bath. After 30 min, isobutyric anhydride (17 mL, 100 mmol) was added dropwise and the reaction mixture was stirred for 2.5 h at room temperature. The reaction mixture was then chilled in an ice-bath, 40 mL of cold water was added and let stir for 15 min. Concentrated aqueous NH4OH was added, let stir for another 30 min and rotovapped to give oil with salts. Water was added until all salts dissolved and washed once with equal volume of ether. The product crystallizes immediately in the aqueous layer, which was filtered and dried on vacuum until constant weight to give 5.575 g of 1 (82% yield) as a white solid.

Reference： [1]Patent: US2011/86813,2011,A1 .Location in patent: Page/Page column 33-34

61
C₉₈H₁₂₂FN₄₀O₅₆P₉S [ No CAS ]
[ 890-38-0 ]
[ 869355-51-1 ]
[ 961-07-9 ]
[ 951-77-9 ]
[ 50-89-5 ]
[ 958-09-8 ]

Yield	Reaction Conditions	Operation in experiment
	With Crotalus adamanteus venom phosphodiesterase I; bovine intestinal mucosa alkaline phosphatase; water; magnesium chloride; at 37℃; for 18h;pH 7.0;aq. phosphate buffer; Enzymatic reaction;	General procedure: Column containing solid support with the synthesized oligonucleotide was attached to a syringe containing 2 mL of 0.4 M solution of DBU in anhydr CH3CN. Approx. 0.7 mL of the solution was pushed into the column, replaced by a new portion after 5 min and another one after next 5 min. After total time of 15 min the support was washed with dry CH3CN (10 mL) and dried in vacuo. The dried support was placed into a vial, 1 mL of approx. 22% methanolic ammonia was added and the vial closed tightly. After 3 h at rt the solid was filtered off, washed with methanol and water and the filtrates were evaporated. The residue was dissolved in 0.1 m ammonium acetate (1 mL) and passed through a NAP 25 column. The column was washed with the same solution and 6 fractions of 1.4 mL were collected and checked by UV. The oligomer was present mainly in the fractions 3 and 4, with some residue in 5th fraction. Combined fractions were evaporated, dissolved in H2O/acetonitrile, 95/5, v/v (1 mL) and purified by HPLC (two 500 mul injections, Waters XBridge OST C18 Column, 2.5 mum,10 × 50 mm, phase A = 0.1 M TEAA, B = 0.1 M TEAA/Acetonitrile, 50/50, v/v, flow rate 1 ml/min, T = 40 C, gradient 17-20%B in 10 min, then to 50%B in 5 min. Combined fractions were concentrated to approx. 0.5 mL and desalted by passage through HPLC column. Yields of the oligomers BS3-BS6 see Table 1. The oligomerswere verified by enzymatic digestion, results see Table 3. Enzymatic digestion conditions: 0.2 OD of oligonucleotide in 150 muL of buffer (10 mM KH2PO4, 10 mM MgCl2, pH 7) was digested with alkaline phosphatase bovine intestinal mucosa (27 DEA units, Sigma-Aldrich, BioUltra) and phosphodiesterase I from Crotalus adamanteus venom (0.0055 units, Sigma-Aldrich, Purified) for 18 h at 37 C. The enzyme caused partial deamination of dA to dI (confirmed in model experiment).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6098 - 6106

62
C₉₈H₁₂₂FN₄₀O₅₆P₉S [ No CAS ]
[ 890-38-0 ]
[ 869355-51-1 ]
[ 961-07-9 ]
[ 951-77-9 ]
[ 50-89-5 ]
[ 958-09-8 ]

Yield	Reaction Conditions	Operation in experiment
	With Crotalus adamanteus venom phosphodiesterase I; bovine intestinal mucosa alkaline phosphatase; water; magnesium chloride; at 37℃; for 18h;pH 7.0;aq. phosphate buffer; Enzymatic reaction;	General procedure: Column containing solid support with the synthesized oligonucleotide was attached to a syringe containing 2 mL of 0.4 M solution of DBU in anhydr CH3CN. Approx. 0.7 mL of the solution was pushed into the column, replaced by a new portion after 5 min and another one after next 5 min. After total time of 15 min the support was washed with dry CH3CN (10 mL) and dried in vacuo. The dried support was placed into a vial, 1 mL of approx. 22% methanolic ammonia was added and the vial closed tightly. After 3 h at rt the solid was filtered off, washed with methanol and water and the filtrates were evaporated. The residue was dissolved in 0.1 m ammonium acetate (1 mL) and passed through a NAP 25 column. The column was washed with the same solution and 6 fractions of 1.4 mL were collected and checked by UV. The oligomer was present mainly in the fractions 3 and 4, with some residue in 5th fraction. Combined fractions were evaporated, dissolved in H2O/acetonitrile, 95/5, v/v (1 mL) and purified by HPLC (two 500 mul injections, Waters XBridge OST C18 Column, 2.5 mum,10 × 50 mm, phase A = 0.1 M TEAA, B = 0.1 M TEAA/Acetonitrile, 50/50, v/v, flow rate 1 ml/min, T = 40 C, gradient 17-20%B in 10 min, then to 50%B in 5 min. Combined fractions were concentrated to approx. 0.5 mL and desalted by passage through HPLC column. Yields of the oligomers BS3-BS6 see Table 1. The oligomerswere verified by enzymatic digestion, results see Table 3. Enzymatic digestion conditions: 0.2 OD of oligonucleotide in 150 muL of buffer (10 mM KH2PO4, 10 mM MgCl2, pH 7) was digested with alkaline phosphatase bovine intestinal mucosa (27 DEA units, Sigma-Aldrich, BioUltra) and phosphodiesterase I from Crotalus adamanteus venom (0.0055 units, Sigma-Aldrich, Purified) for 18 h at 37 C. The enzyme caused partial deamination of dA to dI (confirmed in model experiment).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6098 - 6106

63
C₉₉H₁₂₄FN₃₆O₅₈P₉S [ No CAS ]
[ 890-38-0 ]
[ 869355-51-1 ]
[ 961-07-9 ]
[ 951-77-9 ]
[ 50-89-5 ]
[ 958-09-8 ]

Yield	Reaction Conditions	Operation in experiment
	With Crotalus adamanteus venom phosphodiesterase I; bovine intestinal mucosa alkaline phosphatase; water; magnesium chloride; at 37℃; for 18h;pH 7.0;aq. phosphate buffer; Enzymatic reaction;	General procedure: Column containing solid support with the synthesized oligonucleotide was attached to a syringe containing 2 mL of 0.4 M solution of DBU in anhydr CH3CN. Approx. 0.7 mL of the solution was pushed into the column, replaced by a new portion after 5 min and another one after next 5 min. After total time of 15 min the support was washed with dry CH3CN (10 mL) and dried in vacuo. The dried support was placed into a vial, 1 mL of approx. 22% methanolic ammonia was added and the vial closed tightly. After 3 h at rt the solid was filtered off, washed with methanol and water and the filtrates were evaporated. The residue was dissolved in 0.1 m ammonium acetate (1 mL) and passed through a NAP 25 column. The column was washed with the same solution and 6 fractions of 1.4 mL were collected and checked by UV. The oligomer was present mainly in the fractions 3 and 4, with some residue in 5th fraction. Combined fractions were evaporated, dissolved in H2O/acetonitrile, 95/5, v/v (1 mL) and purified by HPLC (two 500 mul injections, Waters XBridge OST C18 Column, 2.5 mum,10 × 50 mm, phase A = 0.1 M TEAA, B = 0.1 M TEAA/Acetonitrile, 50/50, v/v, flow rate 1 ml/min, T = 40 C, gradient 17-20%B in 10 min, then to 50%B in 5 min. Combined fractions were concentrated to approx. 0.5 mL and desalted by passage through HPLC column. Yields of the oligomers BS3-BS6 see Table 1. The oligomerswere verified by enzymatic digestion, results see Table 3. Enzymatic digestion conditions: 0.2 OD of oligonucleotide in 150 muL of buffer (10 mM KH2PO4, 10 mM MgCl2, pH 7) was digested with alkaline phosphatase bovine intestinal mucosa (27 DEA units, Sigma-Aldrich, BioUltra) and phosphodiesterase I from Crotalus adamanteus venom (0.0055 units, Sigma-Aldrich, Purified) for 18 h at 37 C. The enzyme caused partial deamination of dA to dI (confirmed in model experiment).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6098 - 6106

64
C₉₈H₁₂₂FN₄₀O₅₆P₉S [ No CAS ]
[ 890-38-0 ]
[ 869355-51-1 ]
[ 961-07-9 ]
[ 951-77-9 ]
[ 50-89-5 ]
[ 958-09-8 ]

Yield	Reaction Conditions	Operation in experiment
	With Crotalus adamanteus venom phosphodiesterase I; bovine intestinal mucosa alkaline phosphatase; water; magnesium chloride; at 37℃; for 18h;pH 7.0;aq. phosphate buffer; Enzymatic reaction;	General procedure: Column containing solid support with the synthesized oligonucleotide was attached to a syringe containing 2 mL of 0.4 M solution of DBU in anhydr CH3CN. Approx. 0.7 mL of the solution was pushed into the column, replaced by a new portion after 5 min and another one after next 5 min. After total time of 15 min the support was washed with dry CH3CN (10 mL) and dried in vacuo. The dried support was placed into a vial, 1 mL of approx. 22% methanolic ammonia was added and the vial closed tightly. After 3 h at rt the solid was filtered off, washed with methanol and water and the filtrates were evaporated. The residue was dissolved in 0.1 m ammonium acetate (1 mL) and passed through a NAP 25 column. The column was washed with the same solution and 6 fractions of 1.4 mL were collected and checked by UV. The oligomer was present mainly in the fractions 3 and 4, with some residue in 5th fraction. Combined fractions were evaporated, dissolved in H2O/acetonitrile, 95/5, v/v (1 mL) and purified by HPLC (two 500 mul injections, Waters XBridge OST C18 Column, 2.5 mum,10 × 50 mm, phase A = 0.1 M TEAA, B = 0.1 M TEAA/Acetonitrile, 50/50, v/v, flow rate 1 ml/min, T = 40 C, gradient 17-20%B in 10 min, then to 50%B in 5 min. Combined fractions were concentrated to approx. 0.5 mL and desalted by passage through HPLC column. Yields of the oligomers BS3-BS6 see Table 1. The oligomerswere verified by enzymatic digestion, results see Table 3. Enzymatic digestion conditions: 0.2 OD of oligonucleotide in 150 muL of buffer (10 mM KH2PO4, 10 mM MgCl2, pH 7) was digested with alkaline phosphatase bovine intestinal mucosa (27 DEA units, Sigma-Aldrich, BioUltra) and phosphodiesterase I from Crotalus adamanteus venom (0.0055 units, Sigma-Aldrich, Purified) for 18 h at 37 C. The enzyme caused partial deamination of dA to dI (confirmed in model experiment).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6098 - 6106

65
[ 961-07-9 ]
[ 100644-65-3 ]
[ 1396404-77-5 ]

Reference： [1]Synlett,2012,vol. 23,p. 1541 - 1545

66
[ 961-07-9 ]
[ 315-30-0 ]
[ 95087-12-0 ]

Reference： [1]Synlett,2012,vol. 23,p. 1541 - 1545

67
[ 961-07-9 ]
[ 1123-54-2 ]
8-Aza-2'-deoxy-adenosine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With purine nucleoside phosphorylase at 50℃; aq. phosphate buffer; Enzymatic reaction;

Reference： [1]Stepchenko, Vladimir A.; Seela, Frank; Esipov, Roman S.; Miroshnikov, Anatoly I.; Sokolov, Yuri A.; Mikhailopulo, Igor A. [Synlett, 2012, vol. 23, # 10, p. 1541 - 1545]

68
[ 961-07-9 ]
[ 100644-67-5 ]
[ 100644-69-7 ]

Reference： [1]Synlett,2012,vol. 23,p. 1541 - 1545

69
[ 961-07-9 ]
[ 107-02-8 ]
[ 91021-93-1 ]
[ 88847-89-6 ]
[ 91021-92-0 ]

Reference： [1]Analytical Chemistry,2013,vol. 85,p. 3190 - 3197

70
[ 961-07-9 ]
[ 55514-92-6 ]
(R)-8-(2-pyrrolidyl)-2'-deoxyguanosine [ No CAS ]
(S)-8-(2-pyrrolidyl)-2'-deoxyguanosine [ No CAS ]
[ 29049-22-7 ]
[ 88847-89-6 ]
[ 88899-00-7 ]

Yield	Reaction Conditions	Operation in experiment
	In aq. acetate buffer; at 4℃; for 12h;pH 3.7;Acidic conditions; UV-irradiation;	dG (10mM) was irradiated in sodium acetate buffer (3M, pH 3.7) in the presence of NPRO (100mM) in a chamber kept at 4C. Continuous mixing was done during the reaction. UVA irradiation was performed for 12h with 20-W black-light bulbs emitting radiation in the range 300-400nm (Panasonic, Japan). Use of a 4-mm thick glass plate between the light source and the reaction solution excluded radiation of wavelength nm. The UVA dose rate at 360nm on the surface of the solution, measured using a black-ray UV intensity meter (Ultraviolet Products, San Gabriel, CA), was 0.98±0.060mW/cm2. Irradiated samples were fractionated using HPLC (TSK-GEL ODS-80Ts, 21.5mm×300mm) equipped with a photodiode array detector SPP-M 10Avp (Shimadzu, Kyoto). These fractions were analyzed by LC-MSMS (API3000 and API4000, AB SCIEX, MA, USA) with positive mode ESI. The column used was Inertsil ODS-3 (1.0mm×150mm), and the eluent was 5mM ammonium acetate with 0-40% methanol. Co-chromatography with authentic specimen was performed with 10muL of irradiated sample mixed with 1nmol of dX, 1nmol of dO or 2nmol of 8-oxodG. 1H NMR spectra of samples dissolved in dimethylsulfoxide-d6 were recorded on a Unity INOVA AS600 spectrometer (Agilent Technologies, Tokyo) at 600MHz.

Reference： [1]Journal of Photochemistry and Photobiology A: Chemistry,2014,vol. 276,p. 1 - 7

71
[ 1946-82-3 ]
[ 961-07-9 ]
[ 78-98-8 ]
C₂₁H₃₁N₇O₈ [ No CAS ]

Reference： [1]Chemical Research in Toxicology,2014,vol. 27,p. 1019 - 1029

72
[ 961-07-9 ]
spiroiminodihydantoin-2'-deoxyribonucleoside [ No CAS ]
[ 73-40-5 ]
[ 5614-64-2 ]
[ 1309569-79-6 ]
5-carboxamido-5-formamido-2-iminohydantion-2′-deoxyribonucleoside [ No CAS ]
5',8-cyclo-2'-deoxyguanosine [ No CAS ]
[ 88847-89-6 ]
N¹-(β-D-erythro-pentofuranosyl)-5-guanidinohydantoin [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 6996 - 7007
[2]Journal of Organic Chemistry,2015,vol. 80,p. 6996 - 7007

73
[ 961-07-9 ]
spiroiminodihydantoin-2'-deoxyribonucleoside [ No CAS ]
[ 73-40-5 ]
[ 104184-01-2 ]
[ 1309569-79-6 ]
5-carboxamido-5-formamido-2-iminohydantion-2′-deoxyribonucleoside [ No CAS ]
5',8-cyclo-2'-deoxyguanosine [ No CAS ]
[ 88847-89-6 ]
N¹-(β-D-erythro-pentofuranosyl)-5-guanidinohydantoin [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 6996 - 7007

74
[ 961-07-9 ]
spiroiminodihydantoin-2'-deoxyribonucleoside [ No CAS ]
5-carboxamido-5-formamido-2-iminohydantion-2′-deoxyribonucleoside [ No CAS ]
5',8-cyclo-2'-deoxyguanosine [ No CAS ]
[ 88847-89-6 ]
N¹-(β-D-erythro-pentofuranosyl)-5-guanidinohydantoin [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 6996 - 7007

75
[ 961-07-9 ]
C₁₀H₁₃N₅O₆ [ No CAS ]
C₁₀H₁₄N₆O₅ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 711 - 721

76
[ 961-07-9 ]
C₁₀H₁₃N₅O₆ [ No CAS ]
C₁₀H₁₄N₆O₅ [ No CAS ]
C₁₀H₁₄N₆O₅ [ No CAS ]
2,2-Diamino-4-((4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-ylamino)-2H-oxazol-5-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 711 - 721

77
[ 961-07-9 ]
C₁₀H₁₃N₅O₆ [ No CAS ]
C₁₀H₁₄N₆O₅ [ No CAS ]
C₉H₁₅N₅O₅*H⁽¹⁺⁾ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 711 - 721

78
[ 461-89-2 ]
[ 961-07-9 ]
[ 10592-61-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	With Escherichia coli purine nucleoside phosphorylase; Escherichia coli uridine phosphorylase; In aq. phosphate buffer; at 40℃; for 60h;pH 7.0;Enzymatic reaction;	<strong>[461-89-2]6-Azauracil</strong> (106 mg,0.937 mmol) and 2'-deoxyguanosine (376 mg, 1.406 mmol)were suspended in 10 mM K,Na-phosphate buffer (10 mL), UP(238 units) and PNP (11 units) were added and reaction mixture was stirred at 40 C for 60 h. After that time, the HPLC(Sytem A) indicated almost complete transformation of startingbase into nucleoside 3b. Precipitated guanine was filtered off;silica gel (3 mL) was added and the mixture was evaporated todryness. The residue was twice co-evaporated with ethanol(10 mL) and put on the top of silica gel column (2 × 15 cm) that was eluted with chloroform/methanol, 15:1 (v/v). 6-Aza-2?-deoxyuridine (3b, 193 mg, 0.842 mmol, 90%) was obtained ascolorless oil [30,75]. UV (H2O) lambdamax, nm (epsilon, M-1cm-1): 262(4,000) at pH 7.0, 255 (4,300) at pH 10.0, 263 (4,000) atpH 4.0; lambdamin: 231 (1,900) at pH 7.0, 224 (2,300) at pH 10.0, 232(1,900) at pH 4.0. Lit. data [9]: UV (phosphate buffer):lambdamax, nm (epsilon, M-1cm-1): 262 (6,900) at pH 5.0, 258 (6,900) atpH 7.0, 255 (7,200) at pH 9.0; ESIMS (positive ion mode): 252[M + Na]+, 273 [M + 2Na - 2H]+; ESIMS (negative ion mode):228 [M - H]+.

Reference： [1]Beilstein Journal of Organic Chemistry,2016,vol. 12,p. 2588 - 2601

79
[ 932-53-6 ]
[ 961-07-9 ]
[ 13410-30-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	With Escherichia coli thymidine phosphorylase; Escherichia coli purine nucleoside phosphorylase; In aq. phosphate buffer; at 40℃; for 72h;pH 7.0;Enzymatic reaction;	6-Azathymine (100 mg, 0.787 mmol)and 2'-deoxyguanosine (315 mg, 1.18 mmol) were suspended in10 mM K,Na-phosphate buffer (20 mL), TP (390 units) andPNP (400 units) were added and reaction mixture was stirred at40 C for 72 h. After that time HPLC (System A) indicatedalmost complete conversion of starting base into its nucleoside.Precipitated guanine was filtered off and filtrate was evaporated to dryness. The residue was dissolved in methanol, filtratedand to the filtrate silica gel (2 mL) was added. The mixture wasevaporated to dryness and the residue was put on top of a silicagel column (2 × 10 cm) that was eluted with chloroform/methanol, 15:1 (v/v). 6-Azathymidine (153 mg, 0.630 mmol, 80%)was obtained as colorless oil [30,75]. UV (H2O) lambdamax, nm (epsilon,M-1cm-1): 263 (5,300) at pH 4.0, 263(5,300) at pH 7.0, 252(6,000) at pH 10.0; lambdamin: 234 (2,400) at pH 4.0, 234 (2,300) atpH 7.0, 223 (3,800) at pH 10.0. Lit. data [26]: UV lambdamax, nm (epsilon,M-1cm-1): 250 (0.1 N HCl) and 265 (0.1 N NaOH); lambdamin, nm:225 and 235. ESIMS (positive ion mode): 266 [M + Na]+, 282[M + K]+; ESIMS (negative ion mode): 242 (M - H]+.

Reference： [1]Beilstein Journal of Organic Chemistry,2016,vol. 12,p. 2588 - 2601

80
[ 961-07-9 ]
[ 615-76-9 ]
6-aza-2-thiothymidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With Escherichia coli thymidine phosphorylase; Escherichia coli purine nucleoside phosphorylase In aq. phosphate buffer at 40℃; for 72h; Enzymatic reaction;	6-Aza-2-thiothymidine (5b). 2-Thio-6-azathymine (28 mg,0.193 mmol) and 2′-deoxyguanosine (77 mg, 0.288 mmol) weresuspended in 10 mM K,Na-phosphate buffer (15 mL), PNP(274 units) and TP (145 units) were added and the reaction mixture was stirred at 40 °C and the formation of the products wasmonitored by HPLC (System A). After 72 h the reaction ratesignificantly decreased. Precipitated guanine was filtered off;silica gel (2 mL) was added to the filtrate and solvent removedin vacuum. The residue was co-evaporated with ethanol(10 mL) and put on top of silica gel column (2 × 10 cm) thatwas eluted with chloroform/methanol, 30:1 (v/v). 2-Thio-6-azathymidine (5b) was obtained as white powder (25 mg,0.097 mmol, 50%), that was recrystallized from acetonitrile;mp 174-176 °C.UV spectra (H2O): λmax, nm (ε, M-1cm-1): 272 (18,100) and220 (11,900) at pH 7.0; 263 (21,800) and ca. 238 (shoulder; ca.14,000) at pH 10.0, 272 (18,000) and 219 (12,100) at pH 4.0;λmin: 240 (6,400) at pH 7.0, 217 (9,300) at pH 10.0, 240 (5,600)at pH 4.0.

Reference： [1]Stepchenko, Vladimir A.; Miroshnikov, Anatoly I.; Seela, Frank; Mikhailopulo, Igor A. [Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 2588 - 2601]

81
[ 961-07-9 ]
[ 134461-75-9 ]
[ 958-09-8 ]

Yield	Reaction Conditions	Operation in experiment
	With purine nucleoside phosphorylase; phosphoric acid In aq. phosphate buffer at 37℃; for 24h; Enzymatic reaction;	6 (Reference Examples 1 to 28) General procedure: In a 1.5 mL tube, 50 μL (pH 6.8) of a phosphate buffer solution,Raw materials Nucleoside compound 50 mM (each manufactured by Sigma),The target nucleoside compound base (see Table 2) 50 mM,Nucleoside phosphorylase (thymidine phosphorylase,Purine nucleoside phosphorylase, each manufactured by Sigma), 950 μL of waterWas obtained. The final concentration of phosphoric acid and the amount of enzyme are listed in Table 2.The mixture was allowed to react in a warm water bath at 37 ° C. for 24 hours,A small amount of the mixed solution after the reaction was separated and measured by HPLC,The amount of target nucleoside compound produced was confirmed.Table 2 shows the compound used in the reaction,And raw material nucleoside compound(Mol%) of the nucleoside compound to be produced.

Reference： [1]Current Patent Assignee: SHIBAURA INSTITUTE OF TECHNOLOGY; MITSUBISHI CHEMICAL HOLDINGS CORPORATION - JP2015/160832, 2015, A Location in patent: Paragraph 0032-0033

82
[ 73-40-5 ]
[ 958-09-8 ]
[ 961-07-9 ]

Yield	Reaction Conditions	Operation in experiment
	With purine nucleoside phosphorylase; phosphoric acid; In aq. phosphate buffer; at 37℃; for 24h;pH 6.8;Enzymatic reaction;	General procedure: In a 1.5 mL tube, 50 muL (pH 6.8) of a phosphate buffer solution,Raw materials Nucleoside compound 50 mM (each manufactured by Sigma),The target nucleoside compound base (see Table 2) 50 mM,Nucleoside phosphorylase (thymidine phosphorylase,Purine nucleoside phosphorylase, each manufactured by Sigma), 950 muL of waterWas obtained. The final concentration of phosphoric acid and the amount of enzyme are listed in Table 2.The mixture was allowed to react in a warm water bath at 37 C. for 24 hours,A small amount of the mixed solution after the reaction was separated and measured by HPLC,The amount of target nucleoside compound produced was confirmed.Table 2 shows the compound used in the reaction,And raw material nucleoside compound(Mol%) of the nucleoside compound to be produced.

Reference： [1]Patent: JP2015/160832,2015,A .Location in patent: Paragraph 0032-0033

83
[ 961-07-9 ]
[ 4291-63-8 ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 305 - 312

84
[ 961-07-9 ]
[ 890-38-0 ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 305 - 312

85
[ 961-07-9 ]
[ 700-49-2 ]
[ 21679-12-9 ]

Reference： [1]ChemCatChem,2018,vol. 10,p. 4406 - 4416

86
[ 961-07-9 ]
[ 1904-98-9 ]
[ 4546-70-7 ]

Yield	Reaction Conditions	Operation in experiment
	With purine nucleoside 2’-deoxyribosyltransferase from Trypanosoma brucei immobilized on glutaraldehyde-activated MagReSynAmine microspheres In aq. phosphate buffer at 50℃; for 0.333333h; Enzymatic reaction;

Reference： [1]Pérez, Elena; Sánchez-Murcia, Pedro A.; Jordaan, Justin; Blanco, María Dolores; Mancheño, José Miguel; Gago, Federico; Fernández-Lucas, Jesús [ChemCatChem, 2018, vol. 10, # 19, p. 4406 - 4416]

87
[ 961-07-9 ]
[ 638-53-9 ]
(2R,3S,5R)-5-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-2-((tridecanoyloxy)methyl)tetrahydrofuran-3-yl tridecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23%	With dmap; triethylamine; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 20℃; for 16h;	To 2-amino-9-((2R,4^,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-l,9- dihydro-6H-purin-6-one A-11 (2.5 g, 9.36 mmol) in DMF (100 mL, 20 vol) at rt was added <strong>[638-53-9]<strong>[638-53-9]tridecanoic</strong> acid</strong> (10 g, 46.82 mmol), TEA (6.6 mL, 46.82 mmol), DCC (9.65 g, 46.816 mmol) and DMAP (1.14 g, 9.36 mmol). The reaction mixture was stirred at rt for 16 h. The solvent was then evaporated, and the residue was taken in water (200 mL) and extracted with ethyl acetate (4 x 10 mL). The combined organic layer was washed with water (150 mL), brine (150 mL), dried over anhydrous Na2S04; filtered, and concentrated under reduced pressure. The residue was purified by silica gel (100-200 mesh) chromatography and further purified by trituration with MeOH to afford (2R,3^,5R)-5-(2-amino-6-oxo-l,6-dihydro-9H-purin-9-yl)-2- ((tridecanoyloxy)methyl)tetrahydrofuran-3-yl tridecanoate (Compound 7) (681 mg, 23%) as a white solid. MS (ESI) m/z 660.6 [M+H]+; 1H MR (400 MHz, CDC13) delta 12.1 (br s, 1H), 7.71 (s, 1H), 6.32-6.2 (m, 3H), 5.39 (d, J= 6 Hz, 1H), 4.46-4.28 (m, 3H), 2.9-2.82 (m, 1H), 2.55-2.48 (m, 1H), 2.35 (q, J = 7.2 Hz, 1H), 1.69-1.56 (m, 4H), 1.38-1.15 (m, 37H), 0.91-0.84 (m, 6H).

Reference： [1]Patent: WO2019/169324,2019,A1 .Location in patent: Paragraph 00175

88
[ 186393-31-7 ]
[ 961-07-9 ]
R,R 6-(3,4-pyrrolidinediol)-2′-deoxyguanosine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide

Reference： [1]Seneviratne, Uthpala; Wickramaratne, Susith; Kotandeniya, Delshanee; Groehler, Arnold S.; Geraghty, Robert J.; Dreis, Christine; Pujari, Suresh S.; Tretyakova, Natalia Y. [Medicinal Chemistry Research, 2021, vol. 30, # 2, p. 483 - 499]

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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. 961-07-9 ] {[proInfo.proName]}

Quality Control of [ 961-07-9 ]

Related Doc. of [ 961-07-9 ]

Product Details of [ 961-07-9 ]

Calculated chemistry of [ 961-07-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 961-07-9 ]

Application In Synthesis of [ 961-07-9 ]

[ 961-07-9 ] Synthesis Path-Upstream 1~4

[ 961-07-9 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry