tert-butyl (2R,3S,5R)-2-[(1R,2S)-1-(acetylamino)-2,3-dihydroxypropyl]-5-cyano-3-[(Z)-1-propenyl]-1-pyrrolidinecarboxylate -Drug Synthesis Database

【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.

参考文献中间体

合成目标

【1】 Inhibitors of neuraminidases. WO 0128996 .

中间体序号	中间体编号	品名	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