4-nitrobenzyl (5R)-3-[[2-(acetamido)ethyl]sulfanyl]-6-[(E)ethylidene]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】20065

【品名】4-nitrobenzyl (5R)-3-[[2-(acetamido)ethyl]sulfanyl]-6-[(E)ethylidene]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

【CA登记号】

【分子式】C₂₀H₂₁N₃O₆S

【分子量】431.46936

【元素组成】C 55.67% H 4.91% N 9.74% O 22.25% S 7.43%

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：(XLV)

5) The esterification of olivanic acid MM-17880 (XLI) with 4-nitrobenzyl chloride (XLII) gives the corresponding ester (XLIII), which is ethoxylated with triethyloxonium tetrafluoroborate yielding the ethyl sulfate (XLIV). Elimination of sulfuric acid affords the ethylidene derivative (XLV), which is finally reduced to PS-5 4-nitrobenzyl ester (XV) by means of NaBH4.

参考文献中间体

合成目标

【1】 Corbett, D.F.; Eglington, A.J.; Conversion of the olivanic acids into antibiotics of the PS-5 type: Use of a new carboxy protecting group. J Chem Soc Chem Commun 1980, 1083-4.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XV)	20035	4-nitrobenzyl (5R,6R)-3-[[2-(acetamido)ethyl]sulfanyl]-6-ethyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate		C₂₀H₂₃N₃O₆S	详情	详情
(XLI)	20061	3-[[2-(acetamido)ethyl]sulfanyl]-7-oxo-6-[1-(sulfooxy)ethyl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid		C₁₃H₁₈N₂O₈S₂	详情	详情
(XLII)	16866	1-(Bromomethyl)-4-nitrobenzene; para-Nitrobenzyl bromide	100-11-8	C₇H₆BrNO₂	详情	详情
(XLIII)	20063	4-nitrobenzyl 3-[[2-(acetamido)ethyl]sulfanyl]-7-oxo-6-[1-(sulfooxy)ethyl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate		C₂₀H₂₃N₃O₁₀S₂	详情	详情
(XLIV)	20064	4-nitrobenzyl (5R)-3-[[2-(acetamido)ethyl]sulfanyl]-6-[1-[(ethoxysulfonyl)oxy]ethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate		C₂₂H₂₇N₃O₁₀S₂	详情	详情
(XLV)	20065	4-nitrobenzyl (5R)-3-[[2-(acetamido)ethyl]sulfanyl]-6-[(E)ethylidene]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate		C₂₀H₂₁N₃O₆S	详情	详情

Extended Information