4-(2-ethyl-1,3-dioxolan-2-yl)-3-hydroxy-4-methylpentanoic acid -Drug Synthesis Database

【结构式】

【分子编号】52595

【品名】4-(2-ethyl-1,3-dioxolan-2-yl)-3-hydroxy-4-methylpentanoic acid

【CA登记号】

【分子式】C₁₁H₂₀O₅

【分子量】232.2768

【元素组成】C 56.88% H 8.68% O 34.44%

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 (VI) has been obtained as follows: The condensation of the chiral oxazolidinone (I) with the aldehyde (II) gives the chiral ketone (III) as the major product. The cleavage of the chiral auxiliary with LiOOH in THF yields the carboxylic acid (IV), which is deprotected with HCl in THF to afford the oxoacid (V). Finally, the OH group of (V) is silylated with Tbdms-Cl to furnish the target intermediate carboxylic acid (VI).

参考文献中间体

合成目标

【1】 Panicker, B.; et al.; An unusual reversal of stereoselectivity in a boron mediated aldol reaction: Enantioselective synthesis of the C1-C6 segment of the epothilones. Tetrahedron 2000, 56, 40, 7859.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	52572	4-(1-methylethyl)-3-[2-(methylsulfanyl)acetyl]-1,3-oxazolidin-2-one	C₉H₁₅NO₃S	详情	详情
(II)	52593	2-(2-ethyl-1,3-dioxolan-2-yl)-2-methylpropanal	C₉H₁₆O₃	详情	详情
(III)	52594	3-[4-(2-ethyl-1,3-dioxolan-2-yl)-3-hydroxy-4-methylpentanoyl]-4-(1-methylethyl)-1,3-oxazolidin-2-one	C₁₇H₂₉NO₆	详情	详情
(IV)	52595	4-(2-ethyl-1,3-dioxolan-2-yl)-3-hydroxy-4-methylpentanoic acid	C₁₁H₂₀O₅	详情	详情
(V)	52596	3-hydroxy-4,4-dimethyl-5-oxoheptanoic acid	C₉H₁₆O₄	详情	详情
(VI)	43166	(3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-4,4-dimethyl-5-oxoheptanoic acid	C₁₅H₃₀O₄Si	详情	详情

Extended Information