methyl (3S)-3-hydroxytridecanoate -Drug Synthesis Database

【结构式】

【分子编号】41729

【品名】methyl (3S)-3-hydroxytridecanoate

【CA登记号】

【分子式】C₁₄H₂₈O₃

【分子量】244.37452

【元素组成】C 68.81% H 11.55% O 19.64%

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：(I)

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.

参考文献中间体

合成目标

【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