(2S)-2-[(4-methoxybenzyl)oxy]-4-(phenylsulfonyl)-1-butanol -Drug Synthesis Database

【结构式】

【分子编号】63108

【品名】(2S)-2-[(4-methoxybenzyl)oxy]-4-(phenylsulfonyl)-1-butanol

【CA登记号】

【分子式】C₁₈H₂₂O₅S

【分子量】350.43568

【元素组成】C 61.69% H 6.33% O 22.83% S 9.15%

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：(V)

The intermediate carbaldehyde (VI) and Weinreb amide (IX) have been obtained as follows. The reaction of tetrahydropyranyl glycidol (I) with methyl phenylsulfone (II) by means of BuLi in THF gives the secondary alcohol (III), which is protected with Pmb-Cl and NaH in DMF to yield the diether (IV). Selective cleavage of the THP group of (IV) by means of CSA in methanol affords the primary alcohol (V), which is oxidized with (COCl)2 and DMSO in dichloromethane to provide the aldehyde (VI). Further oxidation of (VI) by means of NaClO2 in t-butanol gives the carboxylic acid (VII), which is finally condensed with N,O-dimethylhydroxylamine (VIII) by means of iso-butyl chloroformate in dichloromethane to yield the intermediate Weinreb amide (IX).

参考文献中间体

合成目标

【1】 Ghosh, A.K.; Wang, Y.; Kim, J.T.; Total synthesis of microtubule-stabilizing agent (-)-laulimalide. J Org Chem 2001, 66, 26, 8973.

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)	63105	2-[(2R)oxiranyloxy]tetrahydro-2H-pyran; (2R)oxiranyl tetrahydro-2H-pyran-2-yl ether		C₇H₁₂O₃	详情	详情
(II)	23622	methyl phenyl sulfone; methyl(dioxo)phenyl-lambda(6)-sulfane	3112-85-4	C₇H₈O₂S	详情	详情
(III)	63106	(2S)-4-(phenylsulfonyl)-1-(tetrahydro-2H-pyran-2-yloxy)-2-butanol		C₁₅H₂₂O₅S	详情	详情
(IV)	63107	2-{[(2S)-2-[(4-methoxybenzyl)oxy]-4-(phenylsulfonyl)butyl]oxy}tetrahydro-2H-pyran; (3S)-3-[(4-methoxybenzyl)oxy]-4-(tetrahydro-2H-pyran-2-yloxy)butyl phenyl sulfone		C₂₃H₃₀O₆S	详情	详情
(V)	63108	(2S)-2-[(4-methoxybenzyl)oxy]-4-(phenylsulfonyl)-1-butanol		C₁₈H₂₂O₅S	详情	详情
(VI)	63109	(2S)-2-[(4-methoxybenzyl)oxy]-4-(phenylsulfonyl)butanal		C₁₈H₂₀O₅S	详情	详情
(VII)	63110	(2S)-2-[(4-methoxybenzyl)oxy]-4-(phenylsulfonyl)butanoic acid		C₁₈H₂₀O₆S	详情	详情
(VIII)	13361	(Methoxyamino)methane; N,O-Dimethylhydroxylamine	1117-97-1	C₂H₇NO	详情	详情
(IX)	63111	(2S)-N-methoxy-2-[(4-methoxybenzyl)oxy]-N-methyl-4-(phenylsulfonyl)butanamide		C₂₀H₂₅NO₆S	详情	详情

Extended Information