tert-butyl (3R,4S,5S)-4-[(tert-butoxycarbonyl)(methyl)amino]-3-methoxy-5-methylheptanoate -Drug Synthesis Database

【结构式】

【分子编号】54619

【品名】tert-butyl (3R,4S,5S)-4-[(tert-butoxycarbonyl)(methyl)amino]-3-methoxy-5-methylheptanoate

【CA登记号】

【分子式】C₁₉H₃₇NO₅

【分子量】359.50652

【元素组成】C 63.48% H 10.37% N 3.9% O 22.25%

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 reaction of N-Boc-L-isoleucine (I) with the lithium derivative of tert-butyl acetate (II) by means of CDI in THF gives the beta-ketoester (III), which is reduced with NaBH4 in methanol to yield the desired (R)-alcohol (IV). N- and O-methylation of (IV) by means of LiHMDS and Me-OTf in HMPA/THF affords the fully methylated ester (V), which is finally hydrolyzed with HCO2H to furnish the desired intermediate, the methylated amino acid (VI).

参考文献中间体

合成目标

【1】 Tomioka, K.; et al.; An expeditious synthesis of dolastatin 10. Tetrahedron 1991, 32, 21, 2395.

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)	30009	(2S,3S)-2-[(tert-butoxycarbonyl)amino]-3-methylpentanoic acid	13139-16-7	C₁₁H₂₁NO₄	详情	详情
(II)	15593	[2-(tert-butoxy)-2-oxoethyl]lithium		C₆H₁₁LiO₂	详情	详情
(III)	54617	tert-butyl (4S,5S)-4-[(tert-butoxycarbonyl)amino]-5-methyl-3-oxoheptanoate		C₁₇H₃₁NO₅	详情	详情
(IV)	54618	tert-butyl (3R,4S,5S)-4-[(tert-butoxycarbonyl)amino]-3-hydroxy-5-methylheptanoate		C₁₇H₃₃NO₅	详情	详情
(V)	54619	tert-butyl (3R,4S,5S)-4-[(tert-butoxycarbonyl)(methyl)amino]-3-methoxy-5-methylheptanoate		C₁₉H₃₇NO₅	详情	详情
(VI)	54599	(3R,4S)-4-[(tert-butoxycarbonyl)(methyl)amino]-3-methoxy-5-methylheptanoic acid		C₁₅H₂₉NO₅	详情	详情

Extended Information