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【结 构 式】 
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【分子编号】65154 【品名】2-({[(3-nitro-4-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl]oxy}benzyl)oxy]carbonyl}amino)acetic acid 【CA登记号】 |
【 分 子 式 】C17H20N2O13 【 分 子 量 】460.35148 【元素组成】C 44.35% H 4.38% N 6.09% O 45.18% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：(V)Reaction of methyl 2,3,4-tri-O-acetyl-beta-D-glucuronyl-3-nitrobenzyl alcohol (I) with N,N'-disuccinimidyl carbonate affords the mixed carbonate ester (II), which is further coupled to glycine (III), producing carbamate (IV). Alcoholysis of (IV) with NaOMe in MeOH yields the deacetylated conjugate (V). This is then activated as the pentafluorophenyl ester (VI) upon treatment with pentafluorophenol and DCC.
| 【1】 Rawale, S.; Hrihorczuk, L.M.; Wei, W.-Z.; Zemlicka, J.; Synthesis and biological activity of the prodrug of class I major histocompatibility peptide GILGFVFTL activated by Beta-glucuronidase. J Med Chem 2002, 45, 4, 937. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 65153 | methyl (2S,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-[4-(hydroxymethyl)-2-nitrophenoxy]tetrahydro-2H-pyran-2-carboxylate | C20H23NO13 | 详情 | 详情 | |
| (II) | 65155 | methyl (2S,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{4-[({[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl}oxy)methyl]-2-nitrophenoxy}tetrahydro-2H-pyran-2-carboxylate | C25H26N2O17 | 详情 | 详情 | |
| (III) | 20436 | glycine | 56-40-6 | C2H5NO2 | 详情 | 详情 |
| (IV) | 65156 | 2-({[(3-nitro-4-{[(2S,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl]oxy}benzyl)oxy]carbonyl}amino)acetic acid | C23H26N2O16 | 详情 | 详情 | |
| (V) | 65154 | 2-({[(3-nitro-4-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl]oxy}benzyl)oxy]carbonyl}amino)acetic acid | C17H20N2O13 | 详情 | 详情 | |
| (VI) | 65157 | methyl (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(2-nitro-4-{[({[2-oxo-2-(2,3,4,5,6-pentafluorophenoxy)ethyl]amino}carbonyl)oxy]methyl}phenoxy)tetrahydro-2H-pyran-2-carboxylate | C23H19F5N2O13 | 详情 | 详情 |
Extended Information