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【结 构 式】

【分子编号】15985

【品名】methyl (2R,3S,4S)-3-(acetamido)-4-(acetoxy)-2-[(1S,2R)-1,2,3-tris(acetoxy)propyl]-3,4-dihydro-2H-pyran-6-carboxylate

【CA登记号】

【 分 子 式 】C20H27NO12

【 分 子 量 】473.43392

【元素组成】C 50.74% H 5.75% N 2.96% O 40.55%

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:(XI)

4) The selective deacetylation of 4-O,5-N,7-O,8-O,9-O-pentaacetyl-2,3-didehydro-2-deoxyneuraminic acid (XI) with boron trifluoride ethearate in benzene/methanol gives the 4-deacetyl derivative (XII), which is treated with trifluoromethanesulfonic anhydride in dichloromethane and with sodium azide in DMF to obtain the 4-azido-4-deoxy derivative (XIII). The reduction of (XIII) with H2S in pyridine affords the corresponding 4-amino derivative (XIV), which is finally condensed with S-methylisothiourea in water and saponified through Dowex 50W x 8 in aqueous NH4OH.

1 Von Itzstein, L.M.; Wu, W.-Y.; Phan, T.; Danylec, B.; Derivs. and analogues of 2-deoxy-2,3-didehydro-N-acetyl neuraminic acid and their use as antiviral agents. EP 0786458; WO 9116320 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XI) 15985 methyl (2R,3S,4S)-3-(acetamido)-4-(acetoxy)-2-[(1S,2R)-1,2,3-tris(acetoxy)propyl]-3,4-dihydro-2H-pyran-6-carboxylate C20H27NO12 详情 详情
(XII) 15986 methyl (2R,3R,4S)-3-(acetamido)-4-hydroxy-2-[(1S,2R)-1,2,3-tris(acetoxy)propyl]-3,4-dihydro-2H-pyran-6-carboxylate C18H25NO11 详情 详情
(XIII) 15979 methyl (2R,3R,4S)-3-(acetamido)-4-azido-2-[(1S,2R)-1,2,3-tris(acetoxy)propyl]-3,4-dihydro-2H-pyran-6-carboxylate C18H24N4O10 详情 详情
(XIV) 15988 methyl (2R,3R,4S)-3-(acetamido)-4-amino-2-[(1S,2R)-1,2,3-tris(acetoxy)propyl]-3,4-dihydro-2H-pyran-6-carboxylate C18H26N2O10 详情 详情
(XV) 10272 [[Amino(imino)methyl]sulfanyl]methane 2986-19-8 C2H6N2S 详情 详情
Extended Information