Advanced
Synthetic Studies on Penems and Carbapenems (VII). Compounds Derived by Cleavage of the <TEX>$\beta$</TEX>-Lactam Ring during (Alkylthio) thiocarbonylation of a 4-Mercapto-3-phenylacetamidoazetidin-2-one Derivative
Synthetic Studies on Penems and Carbapenems (VII). Compounds Derived by Cleavage of the $\beta$-Lactam Ring during (Alkylthio) thiocarbonylation of a 4-Mercapto-3-phenylacetamidoazetidin-2-one Derivative
Journal of the Korean Chemical Society. 1989. Oct, 33(5): 545-550
  • Published : October 20, 1989
Download
PDF
Export by style
Article
Author
Metrics
Cited by
About the Authors
Wang, Han Cheol
Lee, Youn Young
Goo, Yang Mo
Chung, Kyoo Hyun

Abstract
When (3R,4R)-1-(1-benzyloxycarbonyl-2-methyl-1-propenyl)-4-mercapto-3-phenylacetamidoazetidin-2-one(8) was reacted with carbon disulfide and alkyl halides in the presence of triethylamine, the ${\beta}$-lactam ring was cleaved to give (Z)-and (E)-1-alkylthio-5-benzyloxycarbonyl-6-methyl-2-phenylacetamido-4-aza-1,5-heptadien-3-one (13-16) or 2-benzyl-4-(3-benzyloxycarbonyl-4-methyl-1-oxo-2-aza-3-pentenyl)thiazole(17).