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【结 构 式】 
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【分子编号】58257 【品名】S-[(2R,3S)-3-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-oxoazetidinyl] 2-chloroethanethioate 【CA登记号】 |
【 分 子 式 】C13H24ClNO3SSi 【 分 子 量 】337.9427 【元素组成】C 46.2% H 7.16% Cl 10.49% N 4.14% O 14.2% S 9.49% Si 8.31% |
合成路线1
该中间体在本合成路线中的序号：(III)In a related method, the 4-acetoxy-azetidinone (I) is reacted with 2-chlorothioacetic acid (II) in the presence of ZnI2 to give the (chloroacetylthio)azetidinone (III). Nitrogen acylation in (III) by means of allyl oxalyl chloride produces (IV), which undergoes ring closure to the penem (V) in the presence of triethyl phosphite in boiling toluene. Displacement of chloride (V) with sarcosinamide (VI) yields adduct (VII). After desilylation of (VII) to (VIII) by means of tetrabutylammonium fluoride, palladium-catalyzed allyl ester cleavage leads to the title compound.
| 【1】 Arcamone, F.M.; et al.; Synthesis and biological activity of the penem antibiotic MEN 10700 and its orally absorbed ester MEN 11505. J Antibiot 2000, 53, 10, 1086. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 11687 | (2R,3R)-3-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-4-oxoazetanyl acetate | C13H25NO4Si | 详情 | 详情 | |
| (II) | 58256 | 2-chloroethanethioic S-acid | C2H3ClOS | 详情 | 详情 | |
| (III) | 58257 | S-[(2R,3S)-3-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-oxoazetidinyl] 2-chloroethanethioate | C13H24ClNO3SSi | 详情 | 详情 | |
| (IV) | 58258 | allyl 2-{(2R,3S)-3-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-[(2-chloroacetyl)sulfanyl]-4-oxoazetidinyl}-2-oxoacetate | C18H28ClNO6SSi | 详情 | 详情 | |
| (V) | 58259 | allyl (5R,6S)-6-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-(chloromethyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate | C18H28ClNO4SSi | 详情 | 详情 | |
| (VI) | 54572 | 2-(methylamino)acetamide | C3H8N2O | 详情 | 详情 | |
| (VII) | 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 | |
| (VIII) | 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 |