百科

齐多夫定

齐多夫定

CAS号：30516-87-1

英文名：zidovudine

分子式

C10H13N5O4

熔点

113-115°C(lit.)

密度

分子量

267.241

沸点

溶解度

1-5 g/100 mL at 17 ºC

信号词

Warning

危险品标志

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化合物简介

A potent and selective inhibitor of HIV-1 replication.

基本信息

中文名称

齐多夫定

英文名称

zidovudine

中文别名

3’-叠氮-3’-脱氧胸苷、3\'-叠氮脱氧胸苷、1-(3-叠氮基-2,3-二脱氧-β-D-呋喃核糖基)胸腺嘧啶、3\'-叠氮-3\'-脱氧胸苷、叠氮胸苷

英文别名

Retrovis、bwa509u、Azitidin、1-(3-Azido-2,3-dideoxy-β-D-ribofuranosyl)thymine、azidothymidine、ZVD、retrovir、3\'-azido-3\'-droxythymidine、ZDV、Timazid、1-(3-Azido-2,3-Dideoxy-Beta-D-Ribofuranosyl)Thymine、BE-AS09U、Azidothymidine、3\'-Azido-3\'-deoxythymidine、AZT、Zidovudine

CAS号

30516-87-1

分子式

C10H13N5O4

分子量

267.241

精确质量

267.097

PSA

134.07

LOGP

-0.74354

编号系统

MDL号

MFCD00006536

物化性质

外观与性状

白色至灰白色晶体

熔点

113-115°C(lit.)

折射率

47 ° (C=1, H2O)

水溶解性

1-5 g/100 mL at 17 ºC

储存条件

通风低温干燥

安全信息

RTECS号

XP2072000

安全说明

S36/37/39-S45

危险类别码

R40

WGK Germany

3

海关编码

2933990090

危险品标志

Xn

信号词

Warning

危险性描述

H351

危险性防范说明

P281

危险标志

GHS08

生产方法及用途

生产方法

胸腺嘧啶脱氧核苷和三苯基膦溶于二甲基甲酰胺中,缓慢滴入对甲氧基苯甲酸和偶氮二甲酸二乙酯(DEAD)溶于二甲基甲酰胺所成的溶液,在室温下搅拌后,再补加三苯基膦和DEAD。搅拌反应后,将反应液倒入乙醚,在0℃下放置过夜。过滤出的固体用小量乙醚洗,干燥,得酯化的氧桥物,收率84.1%。该氧桥物和叠氮钠在二甲基甲酰胺中,于125℃搅拌。冷到室温,将其倒入5%盐酸中,用醋酸乙酯提取。提取液用20%氯化钠溶液洗至中性,干燥,浓缩,真空干燥得叠氮衍生物,收率81.8%。叠氮衍生物和甲醇钠的甲醇溶液,在室温下搅拌后放置过夜。加入水,减压蒸去溶剂,再加水。用乙醚提取,往分出的水层中加入饱和氯化钠,放置过夜。冷至0℃过滤,滤饼用小量乙醇洗后,用水溶解,并用稀盐酸酸化至Ph=2。减压蒸除水,20%氯化钠洗,干燥,得类白色的齐多夫定固体,收率89.0%,熔点119.0～122.0℃。

用途

多夫定与其他抗—逆转录病毒药物联合使用，用于治疗人类免疫缺陷性病毒（HIV）感染。

合成路线

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3'-叠氮基-3'-脱氧-5'-O-三苯甲基胸苷

3'-叠氮基-3'-脱氧-5'-O-三苯甲基胸苷

齐多夫定

海关数据

共找到1个国家海关数据 >

国家/地区名称	海关编码	更新时间	操作
中国	2933990090	2019-03	查看

上游原料

共找到90个上游原料 >

3'-azido-3'-deoxy-5'-O-thexyldimethylsilylthymidine

3'-azido-3'-deoxy-5'-O-thexyldimethylsilylthymidine

4,5-O-cyclohexylidene-2,3-dideoxy-aldehydo-D-glycero-trans-pent-2-enose

4,5-O-cyclohexylidene-2,3-dideoxy-aldehydo-D-glycero-trans-pent-2-enose

(2R,3R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-5-methoxytetrahydrofuran-3-yl trifluoromethanesulfonate

(2R,3R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-5-methoxytetrahydrofuran-3-yl trifluoromethanesulfonate

4,5-O-cyclohexylidene-2,3-dideoxy-3-azido-aldehydo-D-glycero-pentanose

4,5-O-cyclohexylidene-2,3-dideoxy-3-azido-aldehydo-D-glycero-pentanose

(2S,3S)-3-azido-5,5-bis(benzyloxy)pentane-1,2-diol

(2S,3S)-3-azido-5,5-bis(benzyloxy)pentane-1,2-diol

[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxy-oxophosphanium

[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxy-oxophosphanium

下游产品

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3’-叠氮-2’,3’-双脱氧腺苷

3’-叠氮-2’,3’-双脱氧腺苷

1-[(2R,4S,5S)-5-(hydroxymethyl)-4-isothiocyanatooxolan-2-yl]-5-methylpyrimidine-2,4-dione

1-[(2R,4S,5S)-5-(hydroxymethyl)-4-isothiocyanatooxolan-2-yl]-5-methylpyrimidine-2,4-dione

O-hexadecyl-O'-(3'-azido-3'-deoxythymidin-5'-yl) phosphonate

O-hexadecyl-O'-(3'-azido-3'-deoxythymidin-5'-yl) phosphonate

[(2S,3S,5S)-3-azido-5-(2,6-diaminopurin-9-yl)oxolan-2-yl]methanol

[(2S,3S,5S)-3-azido-5-(2,6-diaminopurin-9-yl)oxolan-2-yl]methanol

1-[(2R,4S,5S)-4-azido-5-(dichlorophosphoryloxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione

1-[(2R,4S,5S)-4-azido-5-(dichlorophosphoryloxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione

[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoate

[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoate

上游原料

3'-azido-3'-deoxy-5'-O-thexyldimethylsilylthymidine 4,5-O-cyclohexylidene-2,3-dideoxy-aldehydo-D-glycero-trans-pent-2-enose (2R,3R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-5-methoxytetrahydrofuran-3-yl trifluoromethanesulfonate 4,5-O-cyclohexylidene-2,3-dideoxy-3-azido-aldehydo-D-glycero-pentanose (2S,3S)-3-azido-5,5-bis(benzyloxy)pentane-1,2-diol [(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxy-oxophosphanium methyl 2-deoxy-3,5-O-isopropylidene-αβ-D-threo-pentafuranoside ethyl (E)-5,5-bis(benzyloxy)pent-2-enoate (S)-(-)-5-羟甲基-2(5H)-呋喃酮 5,5-Dibenzyloxy-2E-penten-1-ol methyl 3,5-O-isopropylidene-2-O-<(methylthio)-thiocarbonyl>-α-D-xylofuranoside 5-苯甲酰基-3-乙烷磺酰基-2-溴胸苷 3'-叠氮基-3'-脱氧-5'-胸苷酸 2-(((2S,3S,5R)-3-azido-5-(phenylthio)tetrahydrofuran-2-yl)methoxy)-4-methoxy-5-methylpyrimidine 1-O-acetyl-3-azido-2,3-dideoxy-5-O-(tert-butyldimethylsilyl)-α,β-D-erythro-pentofuranose 2-Chloro-4-methoxy-5-methylpyrimidine methyl 5-O-(tert-butyldiphenylsilyl)-2-deoxy-α,β-D-threo-pentofuranoside O-benzyl-O'-(3'-azido-3'-deoxythymidin-5'-yl) phosphonate AZT guanidine salt P-(tert-butyl)-3'-azido-3'-deoxythymidine 5'-hydrogenphosphonate 司他夫定 O-isopropyl-O'-(3'-azido-3'-deoxythymidin-5'-yl) phosphonate 2,3’-脱水胸苷 1-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-4-methoxy-5-methyl-2(1H)-pyrimidinone methyl 3,5-O-isopropylidene-αβ-D-xylofuranoside ((2R,3R)-3-(2,2-bis(benzyloxy)ethyl)oxiran-2-yl)methanol 3'-azido-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)thymidine 5-甲基脲嘧啶 3'-Azido-5'-O-(4-methoxybenzoyl)-3'-deoxythymidine 4(R)-azido-5(S)-[[(tert-butyldimethylsilyl)oxy]methyl]-3,4-dihydro-5H-furan-2-one (2S,3S)-3-azido-5,5-bis(benzyloxy)pentane-1,2-diyl dibenzoate O-cyclohexyl-O'-(3'-azido-3'-deoxythymidin-5'-yl) phosphonate methyl 2-deoxy-αβ-D-threo-pentafuranoside (S)-(+)-3-(2,2-二甲基-1,3-二氧戊环-4-基)-顺式-2-丙烯酸乙酯 adamantan-1-yl (((2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl) phosphonate adamantan-1-yl (((2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl) phosphonate ((2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl neopentyl phosphonate 3'-叠氮基-3'-脱氧-5'-O-三苯甲基胸苷 ((2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-(methylsulfonyloxy)-tetrahydrofuran-2-yl)methyl benzoate 5-O-苯甲酰基-2,3-脱水胸腺嘧啶脱氧核苷 Methyl 5-O-benzoyl-3-O-tosyl-2-deoxy-D-xylofuranoside O-ethyl-O'-(3'-azido-3'-deoxythymidin-5'-yl) phosphonate 5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-L-glyceropentonic acid γ-lactone O,O′-二(三甲基甲硅烷基)胸苷 (+)-(2E,4S)-5-Acetoxy-4-(formyloxy)-2-pentenal 1-[5-O-Benzoyl-3-azido-2,3-dideoxy-α,β-D-erythro-pentofuranosyl]-thymine methyl 3-azido-2,3-dideoxy-5-O-tert-butyldiphenylsilyl-α,β-D-erythro-pentofuranoside 胸苷

下游产品

3’-叠氮-2’,3’-双脱氧腺苷 1-[(2R,4S,5S)-5-(hydroxymethyl)-4-isothiocyanatooxolan-2-yl]-5-methylpyrimidine-2,4-dione O-hexadecyl-O'-(3'-azido-3'-deoxythymidin-5'-yl) phosphonate [(2S,3S,5S)-3-azido-5-(2,6-diaminopurin-9-yl)oxolan-2-yl]methanol 1-[(2R,4S,5S)-4-azido-5-(dichlorophosphoryloxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione [(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoate 5-甲基脲嘧啶 1-[(2R,4S,5S)-5-(羟基甲基)-4-甲基氨基四氢呋喃-2-基]-5-甲基嘧啶-2,4-二酮双十二烃基磷酸 3’-氨基-2’,3’-双脱氧胸苷 5'-(1,4-二氢-1-甲基-3-吡啶基羰基)-3'-叠氮基-3'-脱氧胸苷 3'-叠氮基-3'-脱氧-5'-胸苷酸 1-[(2R,4S,5S)-4-[4,5-bis(hydroxymethyl)triazol-1-yl]-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione dihexadecoxy(oxo)phosphanium [(2S,3S,5R)-3-叠氮基-5-(5-甲基-2,4-二氧代嘧啶-1-基)四氢呋喃-2-基]甲基[(2R,3S,4S,5R,6S)-3,4,5,6-四羟基四氢吡喃-2-基]甲基磷酸氢酯 2-amino-1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidin-4-one 呋喃 [(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl 2-(4-phenylpiperazin-1-yl)acetate 甲醇 [(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl 2-morpholin-4-ylacetate 3'-叠氮基-2,6-二氨基嘌呤-2',3'-二脱氧核糖甙 3'-氨基-2',3'-双脱氧鸟苷二氧化碳 L-胱氨酸 (4S)-4-amino-5-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]-5-oxopentanoic acid 5-O-苯甲酰基-3-叠氮基-3-脱氧胸腺嘧啶脱氧核苷