allyl (4S,6S)-6-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-3-(hydroxymethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】35497

【品名】allyl (4S,6S)-6-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-3-(hydroxymethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

【CA登记号】

【分子式】C₂₀H₃₃NO₅Si

【分子量】395.57126

【元素组成】C 60.73% H 8.41% N 3.54% O 20.22% Si 7.1%

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 oxidation of the hydroxymethyl carbapenem (I) with MnO2 in refluxing dichloromethane gives the corresponding aldehyde (II), which is treated with isopropylmagnesium chloride in THF yielding, after chromatographic separation, the 1(R)-hydroxy-2-methylpropyl derivative (III). Finally, this compound is deprotected with Pd(PPh3)4 and converted to the sodium salt with sodium 2-ethylhexanoate (SHE).

参考文献中间体

合成目标

【1】 Kim, J.H.; Jeong, H.J.; Kim, B.J.; Kwak, H.J.; Pyun, D.K.; Lee, C.H.; Kim, E.J.; Synthesis and antibacterial activity of 2alpha-functionalized 1beta-methylcarbapenems related to KR-21012. Bioorg Med Chem Lett 2000, 10, 4, 333.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	35497	allyl (4S,6S)-6-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-3-(hydroxymethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	C₂₀H₃₃NO₅Si	详情	详情
(II)	30037	allyl (4S,5R,6S)-6-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-3-formyl-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	C₂₀H₃₁NO₅Si	详情	详情
(III)	35498	allyl (4S,6S)-6-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-3-[(1R)-1-hydroxy-2-methylpropyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	C₂₃H₃₉NO₅Si	详情	详情

Extended Information