NEW MATERIAL:A compound (salt) of formula I {R1 is (substituted) phenyl, nitrogen-containing heterocyclic ring group which may have O or S as a hetero atom or a group of formula II [R3 is (substituted) phenyl; R4 and R5 are H, lower alkyl or (substituted) phenyl]; R2 is H or OH}.
EXAMPLE: 2',4'-Di-O-acetyl-23-acetylthio-23-demycinosyl-23-deoxydesmycosin.
USE: An antimicrobial agent against Gram-positive and Gram-negative bacteria, effective against resistant germs, and veterinary remedy for infection and feed additive.
PROCESS: The OH group at the 23-position in a compound of formula III [R6 is -CHO or a group of formula IV (R10 and R11 are lower alkyl); R8 is H or -OR7; R7 is a protecting group of OH] is sulfonylated with a sulfonyl balide of the formula R9-SO2X (R9 is tolyl or nitrophenyl; X is halogen) to give a sulfonyl compound of formula V, which is then reacted with an alkali metallic salt of thiolacetic acid to give a 23-acetylthio derivative. The resultant acetylthio derivative is then reacted with a halide of the formula R1-Y (Y is halogen).
WATANABE HIDEYUKI
HIRANO TAKAO
SAKAKIBARA HIDEO
