2-[(4R,6R)-2,2-dimethyl-6-(2-nitriloethyl)-1,3-dioxan-4-yl]acetic acid -Drug Synthesis Database

【结构式】

【分子编号】56661

【品名】2-[(4R,6R)-2,2-dimethyl-6-(2-nitriloethyl)-1,3-dioxan-4-yl]acetic acid

【CA登记号】

【分子式】C₁₀H₁₅NO₄

【分子量】213.23344

【元素组成】C 56.33% H 7.09% N 6.57% O 30.01%

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：(VI)

The 6-cyanohexanoic ester (VII), intermediate in the synthesis of 180072 (see intermediate (XLI) in scheme no. 18007204a) has been obtained as follows: the reaction of 1,6-heptadien-4-ol (I) with BuLi, CO2, and I2 in THF gives the cyclic carbonate (II), which is treated with Ts-OH in acetone to yield the acetonide (III). The reaction of the iodine atom of (III) with KCN in hot DMSO affords the nitrile (IV), which is oxidized at the terminal double bond with OsO4 and NaIO4, or O3 and Me2S, to provide the carbaldehyde (V). The oxidation of (V) with CrO3/H2SO4 in acetone gives the carboxylic acid (VI), which is finally esterified with tert-butanol by means of DCC and DMAP in dichloromethane, yielding the target ester intermediate (VII).

参考文献中间体

合成目标

【1】 Radl, S.; et al.; An improved synthesis of 1,1-dimethylethyl 6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate, a key intermediate for atorvastatin synthesis. Tetrahedron Lett 2002, 43, 11, 2087.

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)	56656	1,6-Heptadien-4-ol	2883-45-6	C₇H₁₂O	详情	详情
(II)	56657	(4S,6S)-4-allyl-6-(iodomethyl)-1,3-dioxan-2-one		C₈H₁₁IO₃	详情	详情
(III)	56658	(4S,6S)-4-allyl-6-(iodomethyl)-2,2-dimethyl-1,3-dioxane		C₁₀H₁₇IO₂	详情	详情
(IV)	56659	2-[(4R,6S)-6-allyl-2,2-dimethyl-1,3-dioxan-4-yl]acetonitrile		C₁₁H₁₇NO₂	详情	详情
(V)	56660	2-[(4R,6R)-2,2-dimethyl-6-(2-oxoethyl)-1,3-dioxan-4-yl]acetonitrile		C₁₀H₁₅NO₃	详情	详情
(VI)	56661	2-[(4R,6R)-2,2-dimethyl-6-(2-nitriloethyl)-1,3-dioxan-4-yl]acetic acid		C₁₀H₁₅NO₄	详情	详情
(VII)	15443	tert-Butyl (4R,3R)-6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate；tert-butyl 2-[(4R,6R)-6-(cyanomethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetate	125971-94-0	C₁₄H₂₃NO₄	详情	详情

Extended Information