| 摘要 |
PURPOSE:To provide a compound useful as a synthetic intermediate for 1- substituted carbapenem derivative which is known as an excellent antibacterial agent. CONSTITUTION:The compound of formula I [R<1> is H or OH-protecting group; R<2> is 1-6C alkyl, 1-6C alkoxy, halogen, etc.; R<3> is CYNR<5>R<6> (Y is O or S; R<5> and R<6> are 1-6C alkyl, aryl, aralkyl, etc.); R<4> is H or amino-protecting group)], e.g. (2R)-2-[(3S,4S)--3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-oxo-4- azetidinyl]thiopropionic acid S-(2-diethylaminocarbonylphenyl) ester. The compound of formula I can be produced by reacting a silyl enol ether of formula II (R<8> to R<10> are 1-4C alkyl or phenyl; Z is 0 or S) with an azetidinone derivative of formula III (R<11> is acyloxy, alkylsulfonyl, etc.) in the presence of a Lewis acid (e.g. zinc oxide) in a solvent (e.g. methylene chloride) at -10 to +70 deg.C. |
