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【结 构 式】 
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【分子编号】43637 【品名】(3R,4S,5R)-4-[[tert-butyl(dimethyl)silyl]oxy]-5-(hydroxymethyl)-3-methyl-5-vinyl-2-pyrrolidinone 【CA登记号】 |
【 分 子 式 】C14H27NO3Si 【 分 子 量 】285.45882 【元素组成】C 58.91% H 9.53% N 4.91% O 16.81% Si 9.84% |
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：(LII)Silylation of (L) by treatment with TBSOTf and 2,6-lutidine in CH2Cl2 furnishes (LI), whose benzyl group is removed by means of Na/NH3 in THF to yield (LII). Moffat oxidation of (LII) gives aldehyde (LIII), which is treated with isopropylmagnesium bromide (LIV) in THF to afford a mixture of adducts from which (LV) is chromatographically separated. Treatment of (LV) with TFA/H2O provides (LVI), which is then treated with O3 (DMS workup) and finally oxidized with HOSO2NH2, NaH2PO4 and NaClO2 to yield carboxylic acid (X).
| 【1】 Chida, N.; et al.; Stereoselective total synthesis of (+)-lactacystin from D-glucose. Tetrahedron 1997, 53, 48, 16287. |
| 【2】 Corey, E.J.; Li, W.-D.Z.; Total synthesis and biological activity of lactacystin, omuralide and analogs. Chem Pharm Bull 1999, 47, 1, 1. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (X) | 43590 | (2R,3S,4R)-3-hydroxy-2-[(1S)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxo-2-pyrrolidinecarboxylic acid | C10H17NO5 | 详情 | 详情 | |
| (L) | 43635 | (3R,4S,5R)-5-[(benzyloxy)methyl]-4-hydroxy-3-methyl-5-vinyl-2-pyrrolidinone | C15H19NO3 | 详情 | 详情 | |
| (LI) | 43636 | (3R,4S,5R)-5-[(benzyloxy)methyl]-4-[[tert-butyl(dimethyl)silyl]oxy]-3-methyl-5-vinyl-2-pyrrolidinone | C21H33NO3Si | 详情 | 详情 | |
| (LII) | 43637 | (3R,4S,5R)-4-[[tert-butyl(dimethyl)silyl]oxy]-5-(hydroxymethyl)-3-methyl-5-vinyl-2-pyrrolidinone | C14H27NO3Si | 详情 | 详情 | |
| (LIII) | 43638 | (2S,3S,4R)-3-[[tert-butyl(dimethyl)silyl]oxy]-4-methyl-5-oxo-2-vinyl-2-pyrrolidinecarbaldehyde | C14H25NO3Si | 详情 | 详情 | |
| (LIV) | 33398 | bromo(isopropyl)magnesium | 920-39-8 | C3H7BrMg | 详情 | 详情 |
| (LV) | 43639 | (3R,4S,5R)-4-[[tert-butyl(dimethyl)silyl]oxy]-5-[(1S)-1-hydroxy-2-methylpropyl]-3-methyl-5-vinyl-2-pyrrolidinone | C17H33NO3Si | 详情 | 详情 | |
| (LVI) | 43640 | (3R,4S,5R)-4-hydroxy-5-[(1S)-1-hydroxy-2-methylpropyl]-3-methyl-5-vinyl-2-pyrrolidinone | C11H19NO3 | 详情 | 详情 |
Extended Information