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

【结构式】

【分子编号】30377

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

【CA登记号】

【分子式】C₂₇H₂₃N₂O₁₀P

【分子量】566.460862

【元素组成】C 57.25% H 4.09% N 4.95% O 28.24% P 5.47%

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：(I)

The condensation of 7-oxo-6-(1-hydroxyethyl)-3-(diphenoxyphosphate)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid p-nitrophenyl ester (I) with the bis(trimethylsilyl) derivative of 2-(iminomethylamino)ethanethiol (II) in the presence of base gives p-nitrophenyl ester of MK-0787, protected with a trimethylsilyl group (III), which is finally deprotected by hydrogenolysis.

参考文献中间体

合成目标

【1】 Reamer, R.a.; Sletzinger, M.; Hartner, F.W.; Liu, T.; Shinkai, I.; A direct transformation of bicyclic keto esters to N-formimidoyl thienamycin. Tetrahedron Lett 1982, 23, 47, 4903.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	30377	4-nitrophenyl (5R,6S)-3-[(diphenoxyphosphoryl)oxy]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	C₂₇H₂₃N₂O₁₀P	详情	详情
(II)	30378	N'-(trimethylsilyl)-N-[2-[(trimethylsilyl)sulfanyl]ethyl]iminoformamide	C₉H₂₄N₂SSi₂	详情	详情
(III)	30379	4-nitrophenyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[[2-([[(trimethylsilyl)imino]methyl]amino)ethyl]sulfanyl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	C₂₁H₂₈N₄O₆SSi	详情	详情

Extended Information