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

2',3'-二脱氧鸟苷(85326-06-3)推荐厂家更多厂家(43)

公司名称	手机号/电话	联系人	QQ	询单
北京百灵威科技有限公司	18210857532	翟先生	3650742139	询单
上海源叶生物科技有限公司	15026964105 15026964105	汤思磊	2881489226	询单
江苏永健医药科技有限公司	17701422016	韩经理	3587493084	询单
郑州阿尔法化工有限公司	15324716602 0371-55013243	刘经理	2853979810	询单
湖北云镁科技有限公司	18327059871 027-59206672	方经理	235010015	询单
上海瀚思化工有限公司	18939883912 021-34536277	顾经理	3003949364	询单
上海腾准生物科技有限公司	19821570922 021-34053661	张经理	3003871136	询单
上海绩祥生物科技有限公司	18605105771	李经理	1799924424	询单
上海甄准生物科技有限公司	15800340161 021-68920155	李经理	3001010259	询单
上海甄准生物科技有限公司	15800340161 021-68920155	李经理	3001010259	询单

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

2',3'-二脱氧鸟苷(85326-06-3)相关文献

1. Complexation of antiretroviral nucleosides 2′,3′-dideoxyinosine, 2′,3′-dideoxyadenosine and 2′,3′-dideoxyguanosine with β-cyclodextrin. A 1H NMR study
Bozenna Golankiewicz,G. Perlovich,J. Poznański,J. Sitkowski,the late L. Stefaniak,J. Zeidler,Wojciech Zielenkiewicz J. Chem. Soc. Perkin Trans. 2 1999 2533
2. New therapeutic strategies based on interference with telomeric DNA synthesis of tumor cells to suppress the growth of tumors
Zhongyan Wang,Xiuli Zhao,Yan Liu,Ting Wang,Kexin Li RSC Adv. 2018 8 25001
3. Chemical ligation of an entire DNA origami nanostructure
Nicole Weizenmann,Gerda Scheidgen-Kleyboldt,Jingjing Ye,Cordula B. Krause,Dominik Kauert,Seham Helmi,Christophe Rouillon,Ralf Seidel Nanoscale 2021 13 17556
4. Chemical ligation of an entire DNA origami nanostructure
Nicole Weizenmann,Gerda Scheidgen-Kleyboldt,Jingjing Ye,Cordula B. Krause,Dominik Kauert,Seham Helmi,Christophe Rouillon,Ralf Seidel Nanoscale 2021 13 17556
5. Pyrrolidine analogues of 2′,3′-dideoxynucleosides: synthesis via 9-aminopurines and 1-aminopyrimidines
Michael R. Harnden,Richard L. Jarvest J. Chem. Soc. Perkin Trans. 1 1991 2073
6. Direct effect of heavy ions and electrons on 2′-deoxyguanosine in the solid state
Marina Gromova,Robert Nardin,Jean Cadet J. Chem. Soc. Perkin Trans. 2 1998 1365
7. Chapter 6. Radiation chemistry
J. Butler,B. M. Hoey,A. J. Swallow Annu. Rep. Prog. Chem. Sect. C: Phys. Chem. 1986 83 129