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【结 构 式】

【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