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【结 构 式】 
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【分子编号】52572 【品名】4-(1-methylethyl)-3-[2-(methylsulfanyl)acetyl]-1,3-oxazolidin-2-one 【CA登记号】 |
【 分 子 式 】C9H15NO3S 【 分 子 量 】217.28904 【元素组成】C 49.75% H 6.96% N 6.45% O 22.09% S 14.76% |
合成路线1
该中间体在本合成路线中的序号：(I)The intermediate carboxylic acid (VI) has been obtained as follows: The condensation of the chiral oxazolidinone (I) with the aldehyde (II) gives the chiral ketone (III) as the major product. The cleavage of the chiral auxiliary with LiOOH in THF yields the carboxylic acid (IV), which is deprotected with HCl in THF to afford the oxoacid (V). Finally, the OH group of (V) is silylated with Tbdms-Cl to furnish the target intermediate carboxylic acid (VI).
| 【1】 Panicker, B.; et al.; An unusual reversal of stereoselectivity in a boron mediated aldol reaction: Enantioselective synthesis of the C1-C6 segment of the epothilones. Tetrahedron 2000, 56, 40, 7859. |
| 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) | 52572 | 4-(1-methylethyl)-3-[2-(methylsulfanyl)acetyl]-1,3-oxazolidin-2-one | C9H15NO3S | 详情 | 详情 | |
| (II) | 52593 | 2-(2-ethyl-1,3-dioxolan-2-yl)-2-methylpropanal | C9H16O3 | 详情 | 详情 | |
| (III) | 52594 | 3-[4-(2-ethyl-1,3-dioxolan-2-yl)-3-hydroxy-4-methylpentanoyl]-4-(1-methylethyl)-1,3-oxazolidin-2-one | C17H29NO6 | 详情 | 详情 | |
| (IV) | 52595 | 4-(2-ethyl-1,3-dioxolan-2-yl)-3-hydroxy-4-methylpentanoic acid | C11H20O5 | 详情 | 详情 | |
| (V) | 52596 | 3-hydroxy-4,4-dimethyl-5-oxoheptanoic acid | C9H16O4 | 详情 | 详情 | |
| (VI) | 43166 | (3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-4,4-dimethyl-5-oxoheptanoic acid | C15H30O4Si | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(III)The intermediate carboxylic acid (V) has been obtained as follows: The reaction of the chiral auxiliary oxazolidinone (I) with the oxoaldehyde (II) by means of Bu2B-OTf, DIEA and Raney Ni in dichloromethane gives the oxazolidide (III), which is treated with Tbdms-OTf, yielding the silyl ether (IV), which is easily purified. Elimination of the auxiliary with LiOH and H2O2 in THF/water affords the target carboxylic acid (V).
| 【1】 Valluri, M.; et al.; Total synthesis of epothilone B. Org Lett 2001, 3, 23, 3607. |
| 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) | 52571 | 3-[9-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-7-hydroxy-2,10-dimethyl-6-methylidene-11-(2-methyl-1,3-thiazol-4-yl)-10-undecenoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one | C34H50N2O5SSi | 详情 | 详情 | |
| (II) | 44448 | 2,2-dimethyl-3-oxopentanal | C7H12O2 | 详情 | 详情 | |
| (III) | 52572 | 4-(1-methylethyl)-3-[2-(methylsulfanyl)acetyl]-1,3-oxazolidin-2-one | C9H15NO3S | 详情 | 详情 | |
| (IV) | 52573 | 3-hydroxy-4,4-dimethyl-1-[4-(1-methylethyl)-2-oxo-1,3-oxazolidin-3-yl]-1,5-heptanedione | C15H25NO5 | 详情 | 详情 | |
| (V) | 43166 | (3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-4,4-dimethyl-5-oxoheptanoic acid | C15H30O4Si | 详情 | 详情 |