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【结 构 式】 
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【分子编号】41730 【品名】methyl (3S)-3-(1-methoxy-1-methylethoxy)tridecanoate 【CA登记号】 |
【 分 子 式 】C18H36O4 【 分 子 量 】316.48144 【元素组成】C 68.31% H 11.47% O 20.22% |
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：(III)synthesis of (3S,4S)-3-hexyl-4-[2(S)-hydroxytridecyl]oxetan-2-one (VI), a key intermediate in the synthesis of orlistat has been reported: Reaction of methyl 3(S)-hydroxytetradecanoate (I) with 2-methoxypropene (II) by means of pyridinium p-toluenesulfonate gives the protected ester (III), which is reduced with DIBAL to the aldehyde (IV). Finally, aldehyde (IV) is condensed with the lithium amide-enolate (V) generated from 1-octanoylbenzotriazole and LiHMDS, resulting in a 4:1 mixture of diastereomeric oxetanones (VI) and (VII) separated by flash chromatography.
| 【1】 Wedler, C.; et al.; Synthesis of enantiomerically pure beta-lactones by the tandem aldol - Lactonization. A highly efficient access to (3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridencyl]oxetan-2-one, the key intermediate for the enzyme inhibitors tetrahydrolipstatin and tetrahydroes. J Org Chem 1999, 64, 14, 5301. |
| 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) | 41729 | methyl (3S)-3-hydroxytridecanoate | C14H28O3 | 详情 | 详情 | |
| (II) | 17354 | isopropenyl methyl ether; 2-methoxy-1-propene | 116-11-0 | C4H8O | 详情 | 详情 |
| (III) | 41730 | methyl (3S)-3-(1-methoxy-1-methylethoxy)tridecanoate | C18H36O4 | 详情 | 详情 | |
| (IV) | 41731 | (3S)-3-(1-methoxy-1-methylethoxy)tridecanal | C17H34O3 | 详情 | 详情 | |
| (V) | 41732 | lithium (E)-1-(1H-1,2,3-benzotriazol-1-yl)-1-octen-1-olate | C14H18LiN3O | 详情 | 详情 | |
| (VI) | 41733 | (3S,4S)-3-hexyl-4-[(2S)-2-hydroxydodecyl]-2-oxetanone | C21H40O3 | 详情 | 详情 | |
| (VII) | 41734 | (3R,4R)-3-hexyl-4-[(2S)-2-hydroxydodecyl]-2-oxetanone | C21H40O3 | 详情 | 详情 |
Extended Information