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紫杉醇

紫杉醇

CAS号：33069-62-4
英文名：paclitaxel
分子式
C47H51NO14
熔点
213°C (dec.)(lit.)
密度
1.39g/cm3
分子量
853.906
沸点
957.115ºC at 760 mmHg
溶解度
信号词
危险品标志
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化合物简介
An antineoplastic. Used in the study of structure and function of microtubles into tubulin. Paclitaxel is now used to treat patients with lung, ovarian, breast cancer, head and neck cancer, and advanced forms of Kaposi's sarcoma. Paclitaxel is a mitotic inhibitor used in cancer chemotherapy.
基本信息
中文名称
紫杉醇
英文名称
paclitaxel
中文别名
红豆杉提取物、泰素、特素、紫素、合成紫杉醇
英文别名
taxol a、Capxol、Taxol、TAXOL、taxal、ABI 007、TAXUS、Paclitaxel、Onxal、NK 105、EMPAC、DHP 107
CAS号
33069-62-4
分子式
C47H51NO14
分子量
853.906
精确质量
853.331
PSA
221.29
LOGP
4.1266
编号系统
UNII
P88XT4IS4D
物化性质
外观与性状
白色粉末
密度
1.39g/cm3
沸点
957.115ºC at 760 mmHg
熔点
213°C (dec.)(lit.)
闪点
532.644ºC
折射率
-49 ° (C=1, MeOH)
稳定性
Stable. Incompatible with strong oxidizing agents. Combustible.
储存条件
2-8ºC
安全信息
RTECS号
DA8340700
安全说明
S22; S26; S36/37/39; S45
危险类别码
R40; R41
WGK Germany
3
危险品运输编码
1544
海关编码
2932999021
危险类别
6.1(b)
包装等级
III
危险品标志
Xn
生产方法及用途
生产方法
1.紫杉醇的制造方法有三种。第一种是合成法,第二种是细菌培养法,第三种是从红豆杉中直接分离制取。前两种方法虽已取得重大研究成果,但均未实现产业化,目前从天然或栽培的红豆杉中分离仍是生产紫杉醇的主要途径。其分离过程一般是甲醇或乙醇浸出(或超离界提取)→己烷脱酯→二氯甲烷或氯仿萃取得粗提物→多次硅胶柱层析→制备性HPLC、TLC、HSCCC纯化→重结晶得产品。由于硅胶柱层析很难将紫杉醇与另一衍生物Cephalomannine分开且产品收率低,Kingston等人采用O3选择性氧化Cephalomannine分子中的烯键,然后再经硅胶柱层析将紫杉醇纯化。近年来,采用高分子树脂进行红豆杉粗提物的脱色及分离取得很大进度,克服了原各种分离方法收率低、产量小、成本高、生长周期长等问题。
2. 7-三乙基硅烷10-脱乙酰巴卡亭Ⅲ的制备 在反应瓶中加入10-脱乙酰卡巴亭Ⅲ1.0g(1.8mmol)和无水吡啶100ml,搅拌溶解,在通N2保护下,缓慢滴加三乙基氯硅烷6.7ml(6.0g,40mmol),滴毕#反应液呈黄色#降温至0oC,于0oC下搅拌反应24h.加乙酸乙酯200ml和水200ml,充分搅拌后静置分层,分取有机层,用饱和硫酸铜溶液(300ml
×3),洗涤,直至将过量的吡啶全部除去,用水100ml洗涤,再用饱和NaCl水溶液100ml洗涤,无水Na2SO4干燥,过滤,滤液减压蒸除溶剂,浓缩剩余物经230~400目硅胶-60(Merck)柱色谱纯化,用二氯甲烷/甲醇(体积比99
:1)洗脱#得化合物7-三乙基硅烷10-脱乙酰巴卡亭Ⅲ1.12g,收率79%,mp256~25
7 oC(二氯甲烷/戊烷).
3. 7-三乙基硅烷巴卡亭Ⅲ的制备 在反应瓶中加入化合物7-三乙基硅烷10-脱乙酰巴卡亭Ⅲ1.0g(1.5mmol)和无水吡啶43ml,降温至0oC,搅拌滴加乙酰氯0.6ml,滴毕,仍在0oC下继续搅拌反应20h.加乙酸乙酯和水各50ml,充分搅拌,静置分层,用乙酸乙酯(30ml
×2)提取水相,合并有机相,用饱和硫酸铜溶液洗涤至吡啶完全除去,然后依次序用水洗、饱和氯化钠溶液洗涤. 无水NaSO4干燥,过滤,将滤液减压浓缩,浓缩剩余液经230~400目硅胶-60(Merck)柱色谱纯化[洗脱剂:二氯甲烷/甲醇(体积比99
:1)],得7-三乙基硅烷巴卡亭Ⅲ1.03g, 收率86%,mp253~254oC(二氯甲烷/戊烷).
4. [2aR-[2aα,4β, 4aβ, 6β,9α-(αR*, βS*),11α,12α,12aα,12bα]]-β-(苯甲酰氨基)-α-羟基苯丙酸6,12b-双(乙酰氧基)-12-(苯甲酰氧基)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-十二氢-4,11-二羟基-4a,8,13,13-四甲基-5-氧代-7,11-亚甲基-1H-环癸并 苯并 氧杂丁环-9-基酯(紫杉醇)的合成 在反应瓶中加入化合物7-三乙基硅烷巴卡亭Ⅲ1.0g(1.4mmol)和无水甲苯70ml, 搅拌溶解, 再在搅拌下加入N-苯甲酰-(2R,3S)-3-苯基异丝氨酸[N-benzoyl-(2R,3S)-3-phenylisoserine]1.3g(4.6mmol),再加入碳化双(环己基亚胺)DCC470mg(4.5mmol),搅拌反应5min,后加入二甲基氨基吡啶(DMAP)350mg(2.8mmol)搅拌4min, 加热至75oC,搅拌反应10h.冷却至室温,用适量乙酸乙酯稀释,静置分层,分取有机层,依次用饱和NaHCO3水溶液洗3次,用水洗2次用饱和NaCl水溶液洗涤2次,然后用无水Na2SO4干燥,过滤,将滤液减压浓缩,剩余浓缩液经硅胶柱色谱纯化,得C-7保护的紫杉醇衍生物,将其溶于预先冷至0oC的含0.5%盐酸的乙醇溶液62ml中,于0oC下通N2保护搅拌30h(用TLC跟踪确认衍生物完全消失,反应即达终点,停止反应).反应液用乙酸乙酯450ml稀释,搅拌均匀后,用水洗涤,静置分层.分取有机层,再用水洗涤5次,用饱和NaCl水溶液洗涤2次,然后用无水Na2SO4干燥,过滤,将滤液减压浓缩,经硅胶[230~400目硅胶-60(Merck)]柱色谱纯化[洗脱剂:二氯甲烷/甲醇(体积比90:10)],得含目的产物的洗脱液经后处理后的产物,再将其用含水甲醇结晶,得
9..mg,收率89%,mp194~195 oC.
用途
紫杉醇主要适用于卵巢癌和乳腺癌，对肺癌、大肠癌、黑色素瘤、头颈部癌、淋巴瘤、脑瘤也都有一定疗效。
合成路线
共找到19条合成路线 >
7-α-glucosyloxyacetyl paclitaxel
197013-82-4
7-α-glucosyloxyacetyl paclitaxel
10-脱乙酰基巴卡丁 III
32981-86-5
10-脱乙酰基巴卡丁 III
紫杉醇
33069-62-4
紫杉醇
巴卡丁 III
27548-93-2
巴卡丁 III
海关数据
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海关编码
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操作
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上游原料
共找到214个上游原料 >
3'-N-debenzoyltaxol
133524-70-6
3'-N-debenzoyltaxol
2’-TES-7-TROC-taxol
219780-99-1
2’-TES-7-TROC-taxol
(2S,3aS,3a1S,7S,8aS,11aS,11bR,12R,14aS)-10,10-di-tert-butyl-7-((tert-butyldimethylsilyl)oxy)-6,16,16-trimethyl-2-phenyl-3a,4,7,8,12,13,14,14a-octahydro-11aH-1,3,9,11-tetraoxa-10-sila-3a1,11b:5,8a-dimethanocyclopenta[4,5]cyclodeca[1,2,3-de]naphthalen-12-ol
219780-76-4
(2S,3aS,3a1S,7S,8aS,11aS,11bR,12R,14aS)-10,10-di-tert-butyl-7-((tert-butyldimethylsilyl)oxy)-6,16,16-trimethyl-2-phenyl-3a,4,7,8,12,13,14,14a-octahydro-11aH-1,3,9,11-tetraoxa-10-sila-3a1,11b:5,8a-dimethanocyclopenta[4,5]cyclodeca[1,2,3-de]naphthalen-12-ol
(2S,3aS,5S,9S,9aS,10S,13bS)-6,9a,14,14-tetramethyl-2-phenyl-5,8,9,9a,10,11,12,13b-octahydro-4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxole-5,9,10,13-tetraol
219780-51-5
(2S,3aS,5S,9S,9aS,10S,13bS)-6,9a,14,14-tetramethyl-2-phenyl-5,8,9,9a,10,11,12,13b-octahydro-4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxole-5,9,10,13-tetraol
13-[(2'R,3'S)-3'-benzoylamino-3'-phenyl-2'-hydroxypropinonyl]-7-trichloroacetylbaccatin III
1033962-72-9
13-[(2'R,3'S)-3'-benzoylamino-3'-phenyl-2'-hydroxypropinonyl]-7-trichloroacetylbaccatin III
(3aS,3a1S,7S,8aS,10S,11aS,11bS,14aS)-7-((tert-butyldimethylsilyl)oxy)-6,16,16-trimethyl-10-phenyl-3a,4,7,8,14,14a-hexahydro-11aH-1,3,9,11-tetraoxa-3a1,11b:5,8a-dimethanocyclopenta[4,5]cyclodeca[1,2,3-de]naphthalene-2,12(13H)-dione
219780-80-0
(3aS,3a1S,7S,8aS,10S,11aS,11bS,14aS)-7-((tert-butyldimethylsilyl)oxy)-6,16,16-trimethyl-10-phenyl-3a,4,7,8,14,14a-hexahydro-11aH-1,3,9,11-tetraoxa-3a1,11b:5,8a-dimethanocyclopenta[4,5]cyclodeca[1,2,3-de]naphthalene-2,12(13H)-dione
下游产品
共找到17个下游商品 >
Baccatin III
31077-81-3
Baccatin III
10-乙酰多西他赛
125354-16-7
10-乙酰多西他赛
7-表-10-脱乙酰基紫杉醇
78432-77-6
7-表-10-脱乙酰基紫杉醇
巴卡丁 III
27548-93-2
巴卡丁 III
(2RS,3RS)-3-benzoylamino-3-phenyl-propane-1,2-diol
103150-32-9
(2RS,3RS)-3-benzoylamino-3-phenyl-propane-1,2-diol
(2alpha,3xi,5beta,10beta,13alpha)-4,10-二乙酰氧基-13-{[(2R,3S)-3-(苯甲酰基氨基)-2-{[二甲基(2-甲基-2-丙基)硅烷基]氧基}-3-苯基丙酰基]氧基}-1-羟基-9-氧代-5,20-环氧紫杉-6,11-二烯-2-基苯甲酸酯
165065-02-1
(2alpha,3xi,5beta,10beta,13alpha)-4,10-二乙酰氧基-13-{[(2R,3S)-3-(苯甲酰基氨基)-2-{[二甲基(2-甲基-2-丙基)硅烷基]氧基}-3-苯基丙酰基]氧基}-1-羟基-9-氧代-5,20-环氧紫杉-6,11-二烯-2-基苯甲酸酯
上游原料
3'-N-debenzoyltaxol 2’-TES-7-TROC-taxol (2S,3aS,3a1S,7S,8aS,11aS,11bR,12R,14aS)-10,10-di-tert-butyl-7-((tert-butyldimethylsilyl)oxy)-6,16,16-trimethyl-2-phenyl-3a,4,7,8,12,13,14,14a-octahydro-11aH-1,3,9,11-tetraoxa-10-sila-3a1,11b:5,8a-dimethanocyclopenta[4,5]cyclodeca[1,2,3-de]naphthalen-12-ol (2S,3aS,5S,9S,9aS,10S,13bS)-6,9a,14,14-tetramethyl-2-phenyl-5,8,9,9a,10,11,12,13b-octahydro-4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxole-5,9,10,13-tetraol 13-[(2'R,3'S)-3'-benzoylamino-3'-phenyl-2'-hydroxypropinonyl]-7-trichloroacetylbaccatin III (3aS,3a1S,7S,8aS,10S,11aS,11bS,14aS)-7-((tert-butyldimethylsilyl)oxy)-6,16,16-trimethyl-10-phenyl-3a,4,7,8,14,14a-hexahydro-11aH-1,3,9,11-tetraoxa-3a1,11b:5,8a-dimethanocyclopenta[4,5]cyclodeca[1,2,3-de]naphthalene-2,12(13H)-dione 7-表-10-脱乙酰基紫杉醇 乙酸酐 2'-O-(methoxyacetyl)paclitaxel (2S,3aS,5S,9aS,10S,13aS,13bS)-5-((tert-butyldimethylsilyl)oxy)-10-((2-methoxypropan-2-yl)oxy)-6,9a,14,14-tetramethyl-2-phenyl-13-((trimethylsilyl)methyl)-5,8,10,11,13a,13b-hexahydro-4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-9(9aH)-one (2S,3aS,5S,9aS,10S,13aR,13bS)-5-((tert-butyldimethylsilyl)oxy)-10-hydroxy-6,9a,14,14-tetramethyl-2-phenyl-5,8,9a,10,11,12,13a,13b-octahydro-4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxole-9,13-dione (3aS,5S,9S,9aS,10S,13aS,13bS)-2,2-di-tert-butyl-5-((tert-butyldimethylsilyl)oxy)-9,10-dihydroxy-6,15,15-trimethyl-4,5,8,9,11,12-hexahydro-13bH-3a,7:9a,13a-dimethanobenzo[3,4]cyclodeca[1,2-d][1,3,2]dioxasilol-13(10H)-one (2S,3aS,3a1S,7S,8aS,11aS,11bS,14aS)-10,10-di-tert-butyl-7-((tert-butyldimethylsilyl)oxy)-6,16,16-trimethyl-2-phenyl-3a,4,7,8,14,14a-hexahydro-11aH-1,3,9,11-tetraoxa-10-sila-3a1,11b:5,8a-dimethanocyclopenta[4,5]cyclodeca[1,2,3-de]naphthalen-12(13H)-one 10-脱乙酰基巴卡丁 III 7-O-(2-chloroacetyl)paclitaxel (3aS,3a1S,6aS,7S,8S,10S,13aS)-10-((tert-butyldimethylsilyl)oxy)-7,8-dihydroxy-11,14,14-trimethyl-4,5,7,8,9,10,13,13a-octahydro-1,3-dioxa-3a1,6a:8,12-dimethanocyclodeca[de]naphthalene-2,6(3aH)-dione 紫杉醇缩合物 (2'R,3'S)-2'-ethoxyethyl-7-triethylsilyl taxol 13-O-[[(4S,5R)-3-N-benzoyl-4-phenyloxazolidin-2RS-methoxy-5-yl]carbonyl]-7-O-triethylsilylbaccatin III 2'-O-benzoyl-3'-N-debenzoyl-paclitaxel (3aS,7S,8aS,11aS,12R,14aS)-10,10-di-tert-butyl-7-((tert-butyldimethylsilyl)oxy)-6,15,15-trimethyl-2-phenyl-3a,7,8,11a,12,13,14,14a-octahydro-4H-1,3,9,11-tetraoxa-10-sila-5,8a-methanocyclopenta[4,5]cyclodeca[1,2,3-de]naphthalen-12-ol 7-O-(三乙基硅烷基)浆果赤霉素III 巴卡丁 III 4,5-二甲氧基-2-硝基苄基氯甲酸酯 (2S,3aS,5S,9S,9aS,10S,13aS,13bS)-5-((tert-butyldimethylsilyl)oxy)-9,10-dihydroxy-6,15,15-trimethyl-2-phenyl-4,5,8,9,11,12-hexahydro-13bH-3a,7:9a,13a-dimethanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-13(10H)-one (2S,3aS,5S,9S,9aS,10S,13aR,13bS)-5,9,10-trihydroxy-6,9a,14,14-tetramethyl-2-phenyl-4,5,8,9,9a,10,11,12,13a,13b-decahydro-13H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-13-one (2S,3aS,5S,9aS,10S,13aR,13bS)-5-((tert-butyldimethylsilyl)oxy)-10-((2-methoxypropan-2-yl)oxy)-6,9a,14,14-tetramethyl-9-oxo-2-phenyl-5,8,9,9a,10,11,13a,13b-octahydro-4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-13-yl trifluoromethanesulfonate 4-二甲氨基吡啶 (2S,3aS,5S,9S,9aS,10S,13bS)-5-((tert-butyldimethylsilyl)oxy)-6,9a,14,14-tetramethyl-2-phenyl-5,8,9,9a,10,11,12,13b-octahydro-4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxole-9,10,13-triol (2S,3aS,5S,9aS,10S,12S,13aS,13bS)-5-((tert-butyldimethylsilyl)oxy)-12-chloro-10-((2-methoxypropan-2-yl)oxy)-6,9a,14,14-tetramethyl-13-methylene-2-phenyl-5,8,10,11,12,13,13a,13b-octahydro-4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxol-9(9aH)-one (2S,3aS,5S,9aS,10S,13aR,13bS)-5-((tert-butyldimethylsilyl)oxy)-10-((2-methoxypropan-2-yl)oxy)-6,9a,14,14-tetramethyl-2-phenyl-5,8,9a,10,11,12,13a,13b-octahydro-4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxole-9,13-dione 7-O-(三乙基硅烷基)紫杉醇 7-α-glucosyloxyacetyl paclitaxel 苯甲酰氯 (3aS,3a1S,7S,8aS,11aS,11bS,14aS)-10,10-di-tert-butyl-7-((tert-butyldimethylsilyl)oxy)-6,16,16-trimethyl-3a,4,7,8,14,14a-hexahydro-11aH-1,3,9,11-tetraoxa-10-sila-3a1,11b:5,8a-dimethanocyclopenta[4,5]cyclodeca[1,2,3-de]naphthalene-2,12(13H)-dione 7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III 1-hydroxy-7β-triethylsilyloxy-9-oxo-10β-acetyloxy-5β,20-epoxytax-11-ene-2α,4,13α-triyl 4-acetate 2-benzoate 13-[(2R,3S)-3-benzoylamino-2-triethylsilyloxy-3-phenylpropanoate] 2'-(1-Ethoxyethoxy)-7-triethylsilyltaxol
下游产品
Baccatin III 10-乙酰多西他赛 7-表-10-脱乙酰基紫杉醇 巴卡丁 III (2RS,3RS)-3-benzoylamino-3-phenyl-propane-1,2-diol (2alpha,3xi,5beta,10beta,13alpha)-4,10-二乙酰氧基-13-{[(2R,3S)-3-(苯甲酰基氨基)-2-{[二甲基(2-甲基-2-丙基)硅烷基]氧基}-3-苯基丙酰基]氧基}-1-羟基-9-氧代-5,20-环氧紫杉-6,11-二烯-2-基苯甲酸酯 N-苯甲酰基-(2R,3S)-3-苯基异丝氨酸甲酯 2'-O-(叔-丁基二甲基硅烷基)紫杉醇 7-O-(三乙基硅烷基)紫杉醇 10-脱乙酰基巴卡丁 III 7-表紫杉醇 2'-O-acetyl-7α-paclitaxel 2',7-二[(2,2,2-三氯乙氧基)羰基]紫杉醇 7-表-10-去乙酰基浆果赤霉素III 2,2-dimethyl-1,1-di(propan-2-yloxy)pentan-3-one 2'-乙酰基紫杉醇 2'-O-[(2,2,2,-三氯乙基)氧基]羰基紫杉醇
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