allyl (5R,6S)-6-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-{[(methylsulfonyl)oxy]methyl}-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】58253

【品名】allyl (5R,6S)-6-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-{[(methylsulfonyl)oxy]methyl}-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

【CA登记号】

【分子式】C₁₉H₃₁NO₇S₂Si

【分子量】477.67518

【元素组成】C 47.77% H 6.54% N 2.93% O 23.45% S 13.43% Si 5.88%

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：(II)

The 2-(hydroxymethyl)penem (I) is transformed into the corresponding mesylate (II), which is then condensed with sarcosinamide (III), to afford adduct (IV). The O-silyl group of (IV) is removed by treatment with tetrabutylammonium fluoride, yielding alcohol (V). Finally, the allyl ester group of (V) is cleaved in the presence of palladium and triphenylphosphine to furnish the target carboxylic acid.

参考文献中间体

合成目标

【3】 Altamura, M.; Arcamone, F.M.; Perrotta, E.; Pestellini, V.; Sbraci, P.; Cascio, G. (Lusofarmaco; Menarini Industrie Farma Riunite Srl); Penem derivs., their preparation and pharmaceutical compsns. containing them. EP 0660837; JP 1996501543; WO 9406803 .
【1】 Pestellini, V.; Perrotta, E.; Arcamone, F.; Sbraci, P.; Altamura, M.; 2-Substituted penems with amino acid-related side chains: Synthesis and antibacterial activity of a new series of beta-lactam antibiotics. J Med Chem 1995, 38, 21, 4244.
【2】 Altamura, M.; et al.; Synthesis and antibacterial activity of MEN 10700, a new penem antibiotic. Bioorg Med Chem Lett 1995, 5, 6, 555.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	58252	allyl (5R,6S)-6-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-(hydroxymethyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	C₁₈H₂₉NO₅SSi	详情	详情
(II)	58253	allyl (5R,6S)-6-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-{[(methylsulfonyl)oxy]methyl}-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	C₁₉H₃₁NO₇S₂Si	详情	详情
(III)	54572	2-(methylamino)acetamide	C₃H₈N₂O	详情	详情
(IV)	58254	allyl (5R,6S)-3-{[(2-amino-2-oxoethyl)(methyl)amino]methyl}-6-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	C₂₁H₃₅N₃O₅SSi	详情	详情
(V)	58255	allyl (5R,6S)-3-{[(2-amino-2-oxoethyl)(methyl)amino]methyl}-6-[(1R)-1-hydroxyethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	C₁₅H₂₁N₃O₅S	详情	详情

Extended Information