4-nitrobenzyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[[(2R,3R)-2-([[(2S)-3-methyl-2-([[(4-nitrobenzyl)oxy]carbonyl]amino)butanoyl]amino]methyl)tetrahydro-3-furanyl]sulfanyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】33063

【品名】4-nitrobenzyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[[(2R,3R)-2-([[(2S)-3-methyl-2-([[(4-nitrobenzyl)oxy]carbonyl]amino)butanoyl]amino]methyl)tetrahydro-3-furanyl]sulfanyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

【CA登记号】

【分子式】C₃₅H₄₁N₅O₁₂S

【分子量】755.80304

【元素组成】C 55.62% H 5.47% N 9.27% O 25.4% S 4.24%

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：(XXXI)

A convergent synthesis was further developed. Azide (XII) was reduced to the corresponding amine (XXVIII) employing triethyl phosphite. Hydrolysis of the thioacetate ester of (XXVIII) then gave thiol (XXIX). Coupling of (XXIX) with protected valine succinimidyl ester (XXVI) produced amide (XXX). Condensation of (XXX) with carbapenem phosphate (VIII) yielded adduct (XXXI). The p-nitrobenzyl esters were finally deprotected by catalytic hydrogenation.

参考文献中间体

合成目标

【1】 Lin, Y.I.; Li, Z.; Bitha, P.; Convergent synthesis of oral 1beta-methylcarbapenems. J Antibiot 1999, 52, 7, 643.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VIII)	13224	4-nitrobenzyl (4R,5R,6S)-3-[(diphenoxyphosphoryl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	90776-59-3	C₂₉H₂₇N₂O₁₀P	详情	详情
(XII)	33046	S-[(2R,3R)-2-(azidomethyl)tetrahydro-3-furanyl] ethanethioate		C₇H₁₁N₃O₂S	详情	详情
(XXVI)	33058	4-nitrobenzyl (1S)-1-[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]-2-methylpropylcarbamate		C₁₇H₁₉N₃O₈	详情	详情
(XXVIII)	33060	S-[(2R,3R)-2-(aminomethyl)tetrahydro-3-furanyl] ethanethioate		C₇H₁₃NO₂S	详情	详情
(XXIX)	33061	(2R,3R)-2-(aminomethyl)tetrahydro-3-furanylhydrosulfide; (2R,3R)-2-(aminomethyl)tetrahydro-3-furanthiol		C₅H₁₁NOS	详情	详情
(XXX)	33062	4-nitrobenzyl (1S)-2-methyl-1-[([[(2R,3R)-3-sulfanyltetrahydro-2-furanyl]methyl]amino)carbonyl]propylcarbamate		C₁₈H₂₅N₃O₆S	详情	详情
(XXXI)	33063	4-nitrobenzyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[[(2R,3R)-2-([[(2S)-3-methyl-2-([[(4-nitrobenzyl)oxy]carbonyl]amino)butanoyl]amino]methyl)tetrahydro-3-furanyl]sulfanyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate		C₃₅H₄₁N₅O₁₂S	详情	详情

Extended Information