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【结 构 式】 
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【分子编号】63824 【品名】methyl (5S,7R)-14b-chloro-5-ethyl-7-({[(4-methylphenyl)sulfonyl]oxy}methyl)-3-[(4-nitrophenyl)sulfonyl]-5-[(2,2,2-trifluoroacetyl)oxy]-1,2,3,4,5,6,7,8,10,14b-decahydroazacycloundecino[5,4-b]indole-9-carboxylate 【CA登记号】 |
【 分 子 式 】C36H37ClF3N3O11S2 【 分 子 量 】844.2833096 【元素组成】C 51.21% H 4.42% Cl 4.2% F 6.75% N 4.98% O 20.85% S 7.6% |
合成路线1
该中间体在本合成路线中的序号：(L)Acid-catalyzed deprotection of the N-Boc and O-silyl groups of (XLV) leads to (XLVI). The primary hydroxyl group of (XLVI) is then tosylated to afford (XLVII). Subsequent esterification of the remaining tertiary hydroxyl with trifluoroacetic anhydride and pyridine yields trifluoroacetate (XLVIII). Chlorination of the indole nucleus of (XLVIII) with t-butyl hypochlorite furnishes the chloroindolenine (XLIX). Thisi is then coupled to vindoline (XXIII) in the presence of trifluoroacetic acid to form the bis-indole adduct (L) (8,9).
| 【1】 Yokoshima, S.; Ueda, T.; Kobayashi, S.; Sato, A.; Kuboyama, T.; Tokuyama, H.; Fukuyama, T.; Stereocontrolled total synthesis of (+)-vinblastine. J Am Chem Soc 2002, 124, 10, 2137. |
| 【2】 Schneider, C.; First de novo synthesis of the bisindole alkaloid vinblastine. Angew Chem. Int Ed 2002, 41, 22, 4217. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XXIV) | 63596 | methyl 4-(acetyloxy)-3a-ethyl-5-hydroxy-6-methyl-8-(methyloxy)-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate | C25H32N2O6 | 详情 | 详情 | |
| (XLVI) | 63816 | 10-(tert-butyl) 9-methyl (5S,7R)-7-({[tert-butyl(diphenyl)silyl]oxy}methyl)-5-ethyl-5-hydroxy-3-[(4-nitrophenyl)sulfonyl]-2,3,4,5,6,7,8,9-octahydroazacycloundecino[5,4-b]indole-9,10(1H)-dicarboxylate | C48H59N3O10SSi | 详情 | 详情 | |
| (XLVII) | 63821 | methyl (5S,7R)-5-ethyl-5-hydroxy-7-(hydroxymethyl)-3-[(4-nitrophenyl)sulfonyl]-1,2,3,4,5,6,7,8,9,10-decahydroazacycloundecino[5,4-b]indole-9-carboxylate | C27H33N3O8S | 详情 | 详情 | |
| (XLVIII) | 63822 | methyl (5S,7R)-5-ethyl-5-hydroxy-7-({[(4-methylphenyl)sulfonyl]oxy}methyl)-3-[(4-nitrophenyl)sulfonyl]-1,2,3,4,5,6,7,8,9,10-decahydroazacycloundecino[5,4-b]indole-9-carboxylate | C34H39N3O10S2 | 详情 | 详情 | |
| (XLIX) | 63823 | methyl (5S,7R)-5-ethyl-7-({[(4-methylphenyl)sulfonyl]oxy}methyl)-3-[(4-nitrophenyl)sulfonyl]-5-[(2,2,2-trifluoroacetyl)oxy]-1,2,3,4,5,6,7,8,9,10-decahydroazacycloundecino[5,4-b]indole-9-carboxylate | C36H38F3N3O11S2 | 详情 | 详情 | |
| (L) | 63824 | methyl (5S,7R)-14b-chloro-5-ethyl-7-({[(4-methylphenyl)sulfonyl]oxy}methyl)-3-[(4-nitrophenyl)sulfonyl]-5-[(2,2,2-trifluoroacetyl)oxy]-1,2,3,4,5,6,7,8,10,14b-decahydroazacycloundecino[5,4-b]indole-9-carboxylate | C36H37ClF3N3O11S2 | 详情 | 详情 | |
| (LI) | 63825 | methyl (3aR,4R,5S,5aR,10bR,13aR)-4-(acetyloxy)-3a-ethyl-9-{(5S,7R,9S)-5-ethyl-9-(methoxycarbonyl)-7-({[(4-methylphenyl)sulfonyl]oxy}methyl)-3-[(4-nitrophenyl)sulfonyl]-5-[(2,2,2-trifluoroacetyl)oxy]-1,2,3,4,5,6,7,8,9,10-decahydroazacycloundecino[5,4 | C61H68F3N5O17S2 | 详情 | 详情 |