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【结 构 式】

【分子编号】60196

【品名】9-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-3-hydroxy-N,2,6-trimethyl-N-(methyloxy)-6-nonenamide

【CA登记号】

【 分 子 式 】C19H39NO4Si

【 分 子 量 】373.6085

【元素组成】C 61.08% H 10.52% N 3.75% O 17.13% Si 7.52%

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:(IV)

Preparation of fragment (VIII) is illustrated in Scheme 24509401a. Aldol condensation of aldehyde (I) with (R)-4-benzyl-3-propionyl-2-oxazolidinone (II) mediated by dibutylboron triflate gives the syn aldol adduct (III). This is converted to the Weinreb amide (IV) by treatment with N,O-dimethyl hydroxylamine in the presence of trimethylaluminium. After silylation of the secondary hydroxyl group of (IV), the resultant bis-silyl ether (V) is selectively desilylated at the primary hydroxyl group with p-toluenesulfonic acid and tetrabutylammonium bisulfate, to afford alcohol (VI). Dess-Martin oxidation of (VI) gives the aldehyde (VII), which is then subjected to Corey-Fuchs olefination with CBr4 and PPh3 to produce the gem-dibromo olefin (VIII)

1 Evans, D.A.; Starr, J.T.; A cascade cycloaddition strategy leading to the total synthesis of (-)-FR182877. Angew Chem. Int Ed 2002, 41, 10, 1787.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 60194 7-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-4-methyl-4-heptenal C14H28O2Si 详情 详情
(II) 25713 (4S)-4-benzyl-3-propionyl-1,3-oxazolidin-2-one C13H15NO3 详情 详情
(III) 60195 (4R)-4-benzyl-3-((2R,3S,6E)-9-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-2,6-dimethyl-6-nonenoyl)-1,3-oxazolidin-2-one C27H43NO5Si 详情 详情
(IV) 60196 9-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-3-hydroxy-N,2,6-trimethyl-N-(methyloxy)-6-nonenamide C19H39NO4Si 详情 详情
(V) 60197 3,9-bis{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-N,2,6-trimethyl-N-(methyloxy)-6-nonenamide C25H53NO4Si2 详情 详情
(VI) 60198 3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-9-hydroxy-N,2,6-trimethyl-N-(methyloxy)-6-nonenamide C19H39NO4Si 详情 详情
(VII) 60199 3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-N,2,6-trimethyl-N-(methyloxy)-9-oxo-6-nonenamide C19H37NO4Si 详情 详情
(VIII) 60352 10,10-dibromo-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-N,2,6-trimethyl-N-(methyloxy)-6,9-decadienamide C20H37Br2NO3Si 详情 详情
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