2,3-二脱氧胞啶

2,3-二脱氧胞啶

CAS号：7481-89-2

英文名：zalcitabine

分子式

C9H13N3O3

熔点

217-218°C(lit.)

密度

1.57 g/cm3

分子量

211.218

沸点

415ºC at 760 mmHg

溶解度

5-10 g/100 mL at 19 ºC

信号词

Warning

危险品标志

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化合物简介

Zalcitabine (2′-3′-dideoxycytidine, ddC), also called dideoxycytidine, is a nucleoside analog reverse transcriptase inhibitor (NARTI) sold under the trade name Hivid. Zalcitabine was the third antiretroviral to be approved by the Food and Drug Administration (FDA) for the treatment of HIV/AIDS. It is used as part of a combination regimen.

基本信息

中文名称

2,3-二脱氧胞啶

英文名称

zalcitabine

中文别名

2\',3-双脱氧胞嘧啶核苷、扎西他滨、扎西胞苷、2’,3’-二脱氧胞苷、2\',3\'-二脱氧胞甙、双脱氧胞嘧啶核苷、2\',3\'-二脱氧胞苷、2\',3\'-二脱氧胞啶、2,3-二脱氧胞嘧啶核苷

英文别名

Zalcitibine、ddCyd、ddC、Dideoxycytidine、HIVID、4-amino-1-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one、Cytidine,2\',3\'-dideoxy、[3H]-Zalcitabine、2\',3\'-Dideoxycytidinene、2\',3\'-DIDEOXYCYTIDINE、Zalcitabine、ddC (Antiviral)

CAS号

7481-89-2

分子式

C9H13N3O3

分子量

211.218

精确质量

211.096

PSA

90.37

LOGP

0.0766

编号系统

UNII

6L3XT8CB3I

物化性质

外观与性状

白色至灰白色结晶粉末

密度

1.57 g/cm3

沸点

415ºC at 760 mmHg

熔点

217-218°C(lit.)

闪点

204.8ºC

折射率

78 ° (C=0.5, H2O)

水溶解性

5-10 g/100 mL at 19 ºC

稳定性

Stable. Combustible. Incompatible with strong oxidizing agents.

储存条件

2-8ºC

安全信息

RTECS号

HA3870000

安全说明

S22-S36

危险类别码

R40

WGK Germany

3

海关编码

2934999090

危险品标志

Xn

危险性描述

H351

危险标志

GHS08

信号词

Warning

危险性防范说明

P281

生产方法及用途

生产方法

N-乙酰基胞嘧啶核苷(4g，14mm
o1)在200ml乙腈中回流，在30min内滴加乙酰溴(10ml，0.137m
o1)，加毕再回流3h。蒸出溶剂，剩余物溶于100ml氯仿后，用100ml水洗。蒸去氯仿，剩余物用10ml乙醇重结晶，得2g无色片状结晶的化合物(I)，收率33%，熔点179-180℃(分解)。化合物(I)(1g，2.3mm
o1)、lg碳酸钙、0.2g钯-硫酸钡和50ml 50%甲醇，在25℃和常压下与氢气摇晃1h(吸收60ml氢)。过滤除去结晶，滤液浓缩至干。剩余物溶于10ml 20%氨-甲醇溶液，于5℃下放置过夜。柱层析后再用乙醇重结晶，得34mg无色结晶的扎西他滨，收率7%。

用途

作用于HIV复制的早期，抑制病毒的逆录酶和终止病毒DNA链的复制。用于晚期免疫缺陷病毒感染患者的治疗。抗病毒药，用于抗癌、抗艾滋病毒

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扎西他宾

2,3-二脱氧胞啶

2,3-二脱氧胞啶

上游原料

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[(2S,5R)-5-(4-acetamido-2-oxopyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methyl acetate

[(2S,5R)-5-(4-acetamido-2-oxopyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methyl acetate

扎西他宾

5-({[tert-butyl(dimethyl)silyl]oxy}methyl)tetrahydrofuran-2-yl acetate

5-({[tert-butyl(dimethyl)silyl]oxy}methyl)tetrahydrofuran-2-yl acetate

3'-O-mesyl-N4,O2',O5'-tripivaloylcytidine

3'-O-mesyl-N4,O2',O5'-tripivaloylcytidine

((2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-chlorotetrahydrofuran-2-yl)methyl pivalate

((2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-chlorotetrahydrofuran-2-yl)methyl pivalate

Cytidine, N-acetyl-2',3'-dideoxy-5'-O-[(1,1-dimethylethyl)diphenylsilyl]-

Cytidine, N-acetyl-2',3'-dideoxy-5'-O-[(1,1-dimethylethyl)diphenylsilyl]-

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2’,3’-二脱氧尿苷

2’,3’-二脱氧尿苷

上游原料

[(2S,5R)-5-(4-acetamido-2-oxopyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methyl acetate 扎西他宾 5-({[tert-butyl(dimethyl)silyl]oxy}methyl)tetrahydrofuran-2-yl acetate 3'-O-mesyl-N4,O2',O5'-tripivaloylcytidine ((2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-chlorotetrahydrofuran-2-yl)methyl pivalate 1-(3,5-dimethoxyphenyl)heptadecan-1-ol 2,2-Dimethyl-propionic acid (2R,3S,5R)-3-chloro-5-(4-chloro-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (S)-5,5-dimethoxypentane-1,2-diol N4-acetyl-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-2',3'-dideoxycytidine N4-benzoyl-2'-deoxy-3'-O-mesyl-5'-O-tritylcytidine 5-(羟基甲基)二氢-2(3H)-呋喃酮 (S)-5-羟甲基二氢呋喃-2-酮 N4-benzoyl-2',3'-dideoxy-3'-iodo-5'-O-tritylcytidine ((2S,5R)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl 2-acetoxybenzoate N4,O5'-diacetyl-2',3'-dideoxycytidine 谷氨酸 (5-O-benzoyl-2,3-dideoxy-β-D-glycero-pentofuranosyl)cytosine (S)-(-)-Tetrahydro-5-oxo-2-furancarboxaldehyde N4-acetyl-1-(5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-D-erythro-pentofuranosyl)cytosine 1-[2,3-dideoxy-5-O-(4-phenybenzoyl)-β-D-glycero-pentofuranosyl]-4-(isobutyrylamino)-2(1H)-pyrimidinone*0.25H2O N-乙酰基-5'-O-[(叔丁基)二甲基硅烷基]胞苷 N-[1-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide 2′,3′-二脱氧胸苷 (2R,3R)-3-(2,2-Dimethoxyethyl)oxiranemethanol 5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxycytidine 5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-D-erythro-pentonic acid γ-lactone 2-Acetoxy-benzoic acid (2S,5R)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 2'-脱氧胞嘧啶核苷 2,3-dideoxy-L-arabino-heptono-1,4-lactone (S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-trimethylsilanyloxy-2,3-dihydro-furan 5,5-dimethoxypent-2-en-1-ol (5S)-(5-tert-butyldimethylsilyloxymethyl)furan-2(5H)-one N-苯甲酰-2'-脱氧胞苷 2,2-Dimethyl-propionic acid (2R,3R,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3-chloro-tetrahydro-furan-2-ylmethyl ester tert-butyl(((2S)-5-methoxytetrahydrofuran-2-yl)methoxy)dimethylsilane ((2S,4S,5R)-4-hydroxy-5-(2-oxo-4-pivalamidopyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl pivalate ((2R,3R,5R)-3-chloro-5-(4-chloro-2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl pivalate 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-(phenylselenenyl)-D-erythro-pentafuranose N4-acetyl-5'-O-(tert-butyldimethylsilyl)-2',3'-bis-O-[(methylthio)thiocarbonyl]cytidine N4-acetyl-1-(2,3-dideoxy-β-D-glycero-pentofuranosyl)cytosine N4-acetyl-2',3'-didehydro-2',3'-dideoxycytidine 1-(3-脱氧呋喃戊糖基)胞嘧啶 O5'-(2,2-dimethyl-propionyl)-2'-deoxy-uridine 5'-O-dimethoxytrityl-N4-benzoyl-2'-deoxycytidine N-乙酰胞嘧啶核苷胞苷

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2’,3’-二脱氧尿苷