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【结 构 式】

【分子编号】55167

【品名】tert-butyl (2R)-2-{(S)-{[tert-butyl(dimethyl)silyl]oxy}[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate

【CA登记号】

【 分 子 式 】C21H37NO6Si

【 分 子 量 】427.61342

【元素组成】C 58.99% H 8.72% N 3.28% O 22.45% Si 6.57%

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:(XXIV)

In an alternative synthesis, copper-catalyzed conjugate addition of propenylmagnesium bromide to the chiral pyrrolidone (XXIV) afforded the propenyl pyrrolidinone (XXV). Reduction of the lactam function of (XXV) by means of DIBAL gave the 2-ydroxypyrrolidine (XXVI), which was reacted with trimethylsilyl cyanide and boron trifluoride to provide nitrile (XXVII). Alcohol (XXVIII), obtained by desilylation of (XXVII) with tetrabutylammonium fluoride, was converted to azide (XXIX) upon treatment with DPPA under Mitsunobu conditions. Azide (XXIX) was then reduced to the primary amine (XXX), employing triphenylphosphine in moist THF. Subsequent acylation with Ac2O furnished acetamide (XXXI).

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
(XXIV) 55167 tert-butyl (2R)-2-{(S)-{[tert-butyl(dimethyl)silyl]oxy}[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate C21H37NO6Si 详情 详情
(XXV) 55168 tert-butyl (2R,3S)-2-{(S)-{[tert-butyl(dimethyl)silyl]oxy}[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-5-oxo-3-[(Z)-1-propenyl]-1-pyrrolidinecarboxylate C24H43NO6Si 详情 详情
(XXVI) 55169 tert-butyl (2R,3S)-2-{(S)-{[tert-butyl(dimethyl)silyl]oxy}[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-5-hydroxy-3-[(Z)-1-propenyl]-1-pyrrolidinecarboxylate C24H45NO6Si 详情 详情
(XXVII) 55170 tert-butyl (2R,3S,5R)-2-{(S)-{[tert-butyl(dimethyl)silyl]oxy}[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-5-cyano-3-[(Z)-1-propenyl]-1-pyrrolidinecarboxylate C25H44N2O5Si 详情 详情
(XXVIII) 55171 tert-butyl (2R,3S,5R)-5-cyano-2-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)methyl]-3-[(Z)-1-propenyl]-1-pyrrolidinecarboxylate C19H30N2O5 详情 详情
(XXIX) 55172 tert-butyl (2R,3S,5R)-2-{(R)-azido[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-5-cyano-3-[(Z)-1-propenyl]-1-pyrrolidinecarboxylate C19H29N5O4 详情 详情
(XXX) 55173 tert-butyl (2R,3S,5R)-2-{(R)-amino[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-5-cyano-3-[(Z)-1-propenyl]-1-pyrrolidinecarboxylate C19H31N3O4 详情 详情
Extended Information