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

【结构式】

【分子编号】22687

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

【CA登记号】

【分子式】C₂₂H₂₁N₃O₆S

【分子量】455.49136

【元素组成】C 58.01% H 4.65% N 9.23% O 21.08% S 7.04%

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：(XV)

2) The condensation of 4-nitrobenzyl 6-[1(R)-hydroxyethyl]-2-oxocarbapenam-3-carboxylate (XIV) with diphenyl chlorophosphate as before gives 4-nitrobenzyl 6-[1(R)-hydroxyethyl]-2-(2 pyridyl-methylthio)carbapen-2-em-3-carboxylate (XV), which is quaternized with methyl iodide in acetone to afford the quaternized ester (XVI). Finally, this compound is deprotected by hydrogenolysis with H2 over Pd/C in basic THF.

参考文献中间体

合成目标

【1】 Kim, C.U.; Misco, P.F.; Luh, B.Y.; Hitchcock, M.J.M.; Synthesis and in vitro activity of C-2 quaternary heterocyclic alkylthio carbapenems. J Antibiot 1987, 40, 12, 1707.
【2】 Kim, C.U. (Bristol-Myers Squibb Co.); Carbapenem antibiotics. DE 3334937; GB 2128187; US 4644061 .
【3】 Prous, J.; Castaner, J.; BMY-25174. Drugs Fut 1988, 13, 6, 511.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XI)	22683	2-pyridinylmethylhydrosulfide; 2-pyridinylmethanethiol	C₆H₇NS	详情	详情
(XIV)	22686	4-nitrobenzyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate	C₁₆H₁₆N₂O₇	详情	详情
(XV)	22687	4-nitrobenzyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(2-pyridinylmethyl)sulfanyl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	C₂₂H₂₁N₃O₆S	详情	详情
(XVI)	22688	2-[[((5R,6S)-6-[(1R)-1-hydroxyethyl]-2-[[(4-nitrobenzyl)oxy]carbonyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl)sulfanyl]methyl]-1-methylpyridinium iodide	C₂₃H₂₄IN₃O₆S	详情	详情

Extended Information