PURPOSE: To efficiently obtain the subject compound useful as an intermediate, etc., for synthesizing carbapenem derivatives by reacting a thioester compound with a tri-substituted silyl chloride and then reacting the resultant compound with a specific azetidinone-based compound.
CONSTITUTION: A base is added to a compound expressed by formula I [R2 is 1-6C alkyl, 1-6C alkoxy, halogen, phenyl, etc.; R2 is (substituted)pyridyl or (substituted)quinoline] in the presence of a tri-substituted silyl chloride and made to react therewith to afford a compound expressed by formula II (R5 to R7 are 1-5C alkyl or phenyl), which is then allowed to react with a compound expressed by formula III [R1 is H or protected hydroxyl group; R4 is H or tri-substituted silyl; R8 is 2-4C aliphatic acyloxy, 1-4C alkylsulfinyl, etc.] in the presence of a Lewis acid to provide the objective compound expressed by formula IV.
IWANO YUJI
KOYAMA HIROO
NISHI TAKEHIDE
