4-nitrobenzyl (4S,5R,6S)-6-[(1R)-1-hydroxyethyl]-3-methoxy-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】46696

【品名】4-nitrobenzyl (4S,5R,6S)-6-[(1R)-1-hydroxyethyl]-3-methoxy-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

【CA登记号】

【分子式】C₁₈H₂₀N₂O₇

【分子量】376.36608

【元素组成】C 57.44% H 5.36% N 7.44% O 29.76%

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)

Cyclization of azetidinone (I) by means of catalyst Rh2(OAc)4 in toluol provides carbapenam (II), which is treated with SiO2 in EtOAc to produce epimerization to the alpha-methyl compound (III). Methylation of (III) with diazomethane in dioxane affords carbapenem (IV), which is hydrogenolyzed over Pd/C in EtOAc and finally saponified with KHCO3 in H2O to furnish the desired compound.

参考文献中间体

合成目标

【1】 Weishaupt, R.; Pfaendler, H.R.; Meffert, H.; Synthesis and biological activities of an alpha-methyl and a beta-methyl carbapenem and the corresponding unsubstituted compound. Bioorg Med Chem Lett 2000, 10, 12, 1389.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	38749	4-nitrobenzyl (4R)-2-diazo-4-[(2R,3S)-3-[(1R)-1-hydroxyethyl]-4-oxoazetidinyl]-3-oxopentanoate	C₁₇H₁₈N₄O₇	详情	详情
(II)	37720	4-nitrobenzyl (4R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate	C₁₇H₁₈N₂O₇	详情	详情
(III)	46695	4-nitrobenzyl (4S,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate	C₁₇H₁₈N₂O₇	详情	详情
(IV)	46696	4-nitrobenzyl (4S,5R,6S)-6-[(1R)-1-hydroxyethyl]-3-methoxy-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	C₁₈H₂₀N₂O₇	详情	详情

Extended Information