3-hydroxy-4,4-dimethyl-1-[4-(1-methylethyl)-2-oxo-1,3-oxazolidin-3-yl]-1,5-heptanedione -Drug Synthesis Database

【结构式】

【分子编号】52573

【品名】3-hydroxy-4,4-dimethyl-1-[4-(1-methylethyl)-2-oxo-1,3-oxazolidin-3-yl]-1,5-heptanedione

【CA登记号】

【分子式】C₁₅H₂₅NO₅

【分子量】299.36724

【元素组成】C 60.18% H 8.42% N 4.68% O 26.72%

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：(IV)

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).

参考文献中间体

合成目标

【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	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

Extended Information