2,3,4,5,6-pentafluorophenyl (2S,3S)-2-[[(benzyloxy)carbonyl]amino]-3-methylpentanoate -Drug Synthesis Database

【结构式】

【分子编号】37824

【品名】2,3,4,5,6-pentafluorophenyl (2S,3S)-2-[[(benzyloxy)carbonyl]amino]-3-methylpentanoate

【CA登记号】

【分子式】C₂₀H₁₈F₅NO₄

【分子量】431.359276

【元素组成】C 55.69% H 4.21% F 22.02% N 3.25% O 14.84%

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：(III)

Protection of D-alloisoleucine (I) with Cbz-succinimide afforded benzyl carbamate (II). Activation of the carboxyl group of (II) as the pentafluorophenyl ester (III), followed by condensation with the lithium enolate of methyl acetate, gave beta-ketoester (IV). Stereoselective reduction of (IV) with KBH4 produced alcohol (V) as the major diastereomer. The hydroxyl group of (V) was protected as the triisopropylsilyl ether (VI), and then hydrolysis of the ester group of (VI) yielded carboxylic acid (VII).

参考文献中间体

合成目标

【1】 Liang, B.; et al.; The first total synthesis of (-)-tamadarin A. Org Lett 1999, 1, 8, 1319.

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)	32739	L-2-Amino-3-methylpentanoic acid; L-isoleucine	73-32-5	C₆H₁₃NO₂	详情	详情
(II)	23508	(2S,3S)-2-[[(benzyloxy)carbonyl]amino]-3-methylpentanoic acid	3160-59-6	C₁₄H₁₉NO₄	详情	详情
(III)	37824	2,3,4,5,6-pentafluorophenyl (2S,3S)-2-[[(benzyloxy)carbonyl]amino]-3-methylpentanoate		C₂₀H₁₈F₅NO₄	详情	详情
(IV)	23510	methyl (4S,5S)-4-[[(benzyloxy)carbonyl]amino]-5-methyl-3-oxoheptanoate		C₁₇H₂₃NO₅	详情	详情
(V)	37825	methyl (3S,4S,5S)-4-[[(benzyloxy)carbonyl]amino]-3-hydroxy-5-methylheptanoate		C₁₇H₂₅NO₅	详情	详情
(VI)	37826	methyl (3S,4S,5S)-4-[[(benzyloxy)carbonyl]amino]-5-methyl-3-[(triisopropylsilyl)oxy]heptanoate		C₂₆H₄₅NO₅Si	详情	详情
(VII)	37827	(3S,4S,5S)-4-[[(benzyloxy)carbonyl]amino]-5-methyl-3-[(triisopropylsilyl)oxy]heptanoic acid		C₂₅H₄₃NO₅Si	详情	详情

Extended Information