85326-06-3 (2',3'-二脱氧鸟苷,Dideoxyguanosine)

快速询单

结构式：

2',3'-二脱氧鸟苷MOL文件

CAS号：

85326-06-3

中文名称：

2',3'-二脱氧鸟苷

英文名称：

Dideoxyguanosine

分子式：

C₁₀H₁₃N₅O₃

分子量：

251.241921186447

2',3'-二脱氧鸟苷(85326-06-3)名称与标识符

名称

中文别名：

2',3'-二脱氧鸟苷;2'',3''-二脱氧鸟苷;2 ,3 -二脱氧鸟苷(ddG);2,3-二脱氧鸟苷;2',3'-二脱氧鸟苷(ddG);N-CBZ-反式-L-羟脯氨酸甲酯;2’,3’-二脱氧鸟苷;

英文别名：

2-Amino-9-((2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one;2-Amino-9-[5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one;2',3'-Dideoxyguanosine;2-amino-9-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one;Guanosine, 2',3'-dideoxy-;Dideoxyguanosine;ddGuo;2',3'-Didioxyguanosine;NSC619072;2-amino-9-[(2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H-purin-6-one;deoxy-deoxy-guanosine;2', 3'-Dideoxyguanosine;2'',3''-Dideoxyguanosine;3234AC;AX8012129;2′,3′-Dideoxyguanosine (ACI);

标识符

MDL：

MFCD00057074

InChIKey：

OCLZPNCLRLDXJC-NTSWFWBYSA-N

Inchi：

1S/C10H13N5O3/c11-10-13-8-7(9(17)14-10)12-4-15(8)6-2-1-5(3-16)18-6/h4-6,16H,1-3H2,(H3,11,13,14,17)/t5-,6+/m0/s1

SMILES：

O=C1N=C(N)NC2N([C@H]3CC[C@@H](CO)O3)C=NC1=2

2',3'-二脱氧鸟苷(85326-06-3)物化性质

实验特性

LogP : -0.04710
PSA : 119.05000
沸点 : 632.1°C at 760 mmHg

计算特性

精确分子量 : 251.10200
氢键供体数量 : 3
氢键受体数量 : 5
可旋转化学键数量 : 2
重原子数量 : 18
复杂度 : 388
同位素原子数量 : 0
确定原子立构中心数量 : 2
不确定原子立构中心数量 : 0
确定化学键立构中心数量 : 0
不确定化学键立构中心数量 : 0
共价键单元数量 : 1
疏水参数计算参考值（XlogP） : -0.9
互变异构体数量 : 9
表面电荷 : 0
拓扑分子极性表面积 : 115

2',3'-二脱氧鸟苷(85326-06-3)安全信息

WGK Germany： 3
安全说明： 24/25

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2',3'-二脱氧鸟苷(85326-06-3)合成路线

合成路线：1 步

85326-13-2

_96%

85326-06-3

反应条件：

1.1 Reagents: Ammonia Solvents: Methanol

参考文献：

General syntheses of 2',3'-dideoxynucleosides and 2',3'-didehydro-2',3'-dideoxynucleosides

Chu, C. K.; et al, Journal of Organic Chemistry, 1989, 54(9), 2217-25

合成路线：1 步

122970-35-8

_89%

85326-06-3

反应条件：

1.1 Catalysts: Adenosine deaminase Solvents: Water

参考文献：

Enzymic synthesis of 2',3'-dideoxyguanosine

Nair, Vasu; et al, Synlett, 1991, (10), 753-4

合成路线：1 步

119794-40-0

85326-06-3

反应条件：

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ; rt

参考文献：

Crystal structure of metacavir ethanol solvent compound

Liu, Cai-lian; et al, Huaxue Shiji, 2013, 35(1), 52-54

合成路线：1 步

1477800-54-6

_87%

85326-06-3

反应条件：

1.1 Reagents: Methylamine Solvents: Methanol ; 5 h, rt

参考文献：

Synthesis and Anti-HIV Activity of a Series of 6-Modified 2',3'-dideoxyguanosine and 2',3'-didehydro-2',3'-dideoxyguanosine Analogs

Xie, Lujia; et al, Chinese Journal of Chemistry, 2013, 31(9), 1207-1218

合成路线：1 步

177779-53-2

_77%

85326-06-3

反应条件：

1.1 Reagents: Pyridine , Tetrabutylammonium fluoride Solvents: Tetrahydrofuran

参考文献：

Synthesis and 1H and 13C NMR spectral characteristics of 8-bromo-2',3'-dideoxyguanosine and 8-bromo-2',3'-dideoxyinosine

Zeidler, Joanna; et al, Nucleosides & Nucleotides, 1996, 15(5), 1077-1095

合成路线：1 步

107550-73-2

_37%

85326-06-3

反应条件：

1.1 Catalysts: Adenosine deaminase Solvents: Water ; 48 h, pH 7, 37 °C

参考文献：

Arthrobacter oxydans as a biocatalyst for purine deamination

Medici, Rosario; et al, FEMS Microbiology Letters, 2008, 289(1), 20-26

合成路线：1 步

107550-73-2

_37%

85326-06-3

反应条件：

1.1 Catalysts: Adenosine deaminase ; 48 h

参考文献：

Coupled biocatalysts applied to the synthesis of nucleosides

Medici, Rosario; et al, Nucleic Acids Symposium Series, 2008, 52(1), 541-542

合成路线：1 步

98056-51-0

85326-06-3

反应条件：

1.1 Reagents: Azobisisobutyronitrile , Dibutyltin oxide Solvents: 1,4-Dioxane
1.2 Reagents: Ammonium hydroxide Solvents: Methanol

参考文献：

A novel and efficient preparation of 2',3'-dideoxynucleosides

Prisbe, Ernest J.; et al, Synthetic Communications, 1985, 15(5), 401-9

合成路线：1 步

98056-55-4

85326-06-3

参考文献：

A novel and efficient preparation of 2',3'-dideoxynucleosides

Prisbe, Ernest J.; et al, Synthetic Communications, 1985, 15(5), 401-9

合成路线：2 步

1477800-52-4

85326-06-3

反应条件：

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ; 12 h, 0.4 MPa, rt
2.1 Reagents: Methylamine Solvents: Methanol ; 5 h, rt

参考文献：

Synthesis and Anti-HIV Activity of a Series of 6-Modified 2',3'-dideoxyguanosine and 2',3'-didehydro-2',3'-dideoxyguanosine Analogs

Xie, Lujia; et al, Chinese Journal of Chemistry, 2013, 31(9), 1207-1218

合成路线：2 步

177779-52-1

85326-06-3

反应条件：

1.1 Reagents: Azobisisobutyronitrile , Tributylstannane Solvents: 1,4-Dioxane
2.1 Reagents: Pyridine , Tetrabutylammonium fluoride Solvents: Tetrahydrofuran

参考文献：

Synthesis and 1H and 13C NMR spectral characteristics of 8-bromo-2',3'-dideoxyguanosine and 8-bromo-2',3'-dideoxyinosine

Zeidler, Joanna; et al, Nucleosides & Nucleotides, 1996, 15(5), 1077-1095

合成路线：2 步

2004-07-1

85326-06-3

反应条件：

1.1 -
2.1 Catalysts: Adenosine deaminase Solvents: Water

参考文献：

Enzymic synthesis of 2',3'-dideoxyguanosine

Nair, Vasu; et al, Synlett, 1991, (10), 753-4

合成路线：2 步

反应条件：

1.1 Solvents: Dimethylformamide
1.2 -
2.1 Reagents: Azobisisobutyronitrile , Dibutyltin oxide Solvents: 1,4-Dioxane
2.2 Reagents: Ammonium hydroxide Solvents: Methanol

参考文献：

A novel and efficient preparation of 2',3'-dideoxynucleosides

Prisbe, Ernest J.; et al, Synthetic Communications, 1985, 15(5), 401-9

合成路线：2 步

反应条件：

1.1 Solvents: Dimethylformamide
1.2 -
2.1 -

参考文献：

A novel and efficient preparation of 2',3'-dideoxynucleosides

Prisbe, Ernest J.; et al, Synthetic Communications, 1985, 15(5), 401-9

合成路线：2 步

64350-24-9

85326-06-3

反应条件：

1.1 Reagents: 2-(Acetyloxy)-2-methylpropanoyl bromide Solvents: Acetonitrile , Water ; 1 h, rt
1.2 Reagents: Zinc alloy, base, Zn,Cu ; 10 min, rt
2.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ; rt

参考文献：

Crystal structure of metacavir ethanol solvent compound

Liu, Cai-lian; et al, Huaxue Shiji, 2013, 35(1), 52-54

合成路线：7 步

118-00-3

97-72-3

85326-06-3

反应条件：

1.1 Reagents: Hexamethyldisilazane Solvents: Dimethylformamide
1.2 Solvents: Pyridine
1.3 Reagents: Methanol
2.1 Reagents: Imidazole Solvents: Dimethylformamide
3.1 Solvents: Dimethylformamide
4.1 Reagents: 1,3-Dimethyl-2-phenyl-1,3,2-diazaphospholidine
5.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran
6.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol
7.1 Reagents: Ammonia Solvents: Methanol

参考文献：

General syntheses of 2',3'-dideoxynucleosides and 2',3'-didehydro-2',3'-dideoxynucleosides

Chu, C. K.; et al, Journal of Organic Chemistry, 1989, 54(9), 2217-25

合成路线：3 步

118-00-3

85326-06-3

反应条件：

1.1 -
2.1 -
3.1 Catalysts: Adenosine deaminase Solvents: Water

参考文献：

Enzymic synthesis of 2',3'-dideoxyguanosine

Nair, Vasu; et al, Synlett, 1991, (10), 753-4

合成路线：5 步

118-00-3

85326-06-3

反应条件：

1.1 -
2.1 Solvents: Acetonitrile ; 10 min, -45 °C; 1 h, cooled; 20 h, rt
3.1 Reagents: Zinc Solvents: Dimethylformamide ; 1 h, rt
4.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ; 12 h, 0.4 MPa, rt
5.1 Reagents: Methylamine Solvents: Methanol ; 5 h, rt

参考文献：

Synthesis and Anti-HIV Activity of a Series of 6-Modified 2',3'-dideoxyguanosine and 2',3'-didehydro-2',3'-dideoxyguanosine Analogs

Xie, Lujia; et al, Chinese Journal of Chemistry, 2013, 31(9), 1207-1218

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J. Butler,B. M. Hoey,A. J. Swallow Annu. Rep. Prog. Chem. Sect. C: Phys. Chem. 1986 83 129