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【结 构 式】

【分子编号】55175

【品名】tert-butyl (2R,3S,5R)-2-[(1R,2S)-1-(acetylamino)-2,3-dihydroxypropyl]-5-cyano-3-[(Z)-1-propenyl]-1-pyrrolidinecarboxylate

【CA登记号】

【 分 子 式 】C18H29N3O5

【 分 子 量 】367.44548

【元素组成】C 58.84% H 7.95% N 11.44% O 21.77%

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:(XXXII)

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
Extended Information