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【结 构 式】 
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【分子编号】15986 【品名】methyl (2R,3R,4S)-3-(acetamido)-4-hydroxy-2-[(1S,2R)-1,2,3-tris(acetoxy)propyl]-3,4-dihydro-2H-pyran-6-carboxylate 【CA登记号】 |
【 分 子 式 】C18H25NO11 【 分 子 量 】431.39664 【元素组成】C 50.12% H 5.84% N 3.25% O 40.8% |
合成路线1
该中间体在本合成路线中的序号：(XII)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 |