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【结 构 式】

【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
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