【结 构 式】 |
【分子编号】55179 【品名】tert-butyl (2R,3S,5R)-2-[(1R,2S)-1-(acetylamino)-2-hydroxy-2-methylpentyl]-5-cyano-3-[(Z)-1-propenyl]-1-pyrrolidinecarboxylate 【CA登记号】 |
【 分 子 式 】C21H35N3O4 【 分 子 量 】393.52672 【元素组成】C 64.1% H 8.96% N 10.68% O 16.26% |
合成路线1
该中间体在本合成路线中的序号:(XXXVI)Acidic hydrolysis of the acetonide (XXXI) gave rise to diol (XXXII), which was subjected to oxidative cleavage in the presence of NaIO4, yielding aldehyde (XXXIII). Addition of propylmagnesium chloride to aldehyde (XXXIII) furnished alcohol (XXXIV). After oxidation of (XXXIV) to the corresponding ketone (XXXV), addition of methylmagnesium bromide provided carbinol (XXXVI). The methyl ether (XXXVII) was prepared by alkylation of the sodium alkoxide of (XXXVI) with iodomethane. Finally, hydrolysis of the cyano group of (XXXVII) with concomitant Boc group cleavage under acidic conditions led to the title compound.
【1】 Inhibitors of neuraminidases. WO 0128996 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(XXXI) | 55174 | tert-butyl (2R,3S,5R)-2-{(R)-(acetylamino)[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-5-cyano-3-[(Z)-1-propenyl]-1-pyrrolidinecarboxylate | C21H33N3O5 | 详情 | 详情 | |
(XXXII) | 55175 | tert-butyl (2R,3S,5R)-2-[(1R,2S)-1-(acetylamino)-2,3-dihydroxypropyl]-5-cyano-3-[(Z)-1-propenyl]-1-pyrrolidinecarboxylate | C18H29N3O5 | 详情 | 详情 | |
(XXXIII) | 55176 | tert-butyl (2R,3S,5R)-2-[(1R)-1-(acetylamino)-2-oxoethyl]-5-cyano-3-[(Z)-1-propenyl]-1-pyrrolidinecarboxylate | C17H25N3O4 | 详情 | 详情 | |
(XXXIV) | 55177 | tert-butyl (2R,3S,5R)-2-[(1R)-1-(acetylamino)-2-hydroxypentyl]-5-cyano-3-[(Z)-1-propenyl]-1-pyrrolidinecarboxylate | C20H33N3O4 | 详情 | 详情 | |
(XXXV) | 55178 | tert-butyl (2R,3S,5R)-2-[(1R)-1-(acetylamino)-2-oxopentyl]-5-cyano-3-[(Z)-1-propenyl]-1-pyrrolidinecarboxylate | C20H31N3O4 | 详情 | 详情 | |
(XXXVI) | 55179 | tert-butyl (2R,3S,5R)-2-[(1R,2S)-1-(acetylamino)-2-hydroxy-2-methylpentyl]-5-cyano-3-[(Z)-1-propenyl]-1-pyrrolidinecarboxylate | C21H35N3O4 | 详情 | 详情 | |
(XXXVII) | 55180 | tert-butyl (2R,3S,5R)-2-[(1R,2S)-1-(acetylamino)-2-methoxy-2-methylpentyl]-5-cyano-3-[(Z)-1-propenyl]-1-pyrrolidinecarboxylate | C22H37N3O4 | 详情 | 详情 |