5-Hydroxy-macro:lactone derivs. and glucopyranosyl ether(s) - intermediates for macrolide antibiotics

摘要

Macrolides of formula (I) are new (Bond a is single or double. Bond b is single or double, or is an oxiran-2,3-yl.gp. The dotted lines complete a 16- or 17-membered ring. 2 is either H (Cpds. (Ia)) or the gp. (II). (Cpds. (Ib)). A is carbonyl or RO . R is H, acyl or forosaminyl. R1 is aldehyde gp. protected as cyclic acetal or thioacetal. R2=H or acyl. R3= lower alkyl. R4=H, CH2OH or mycinosyloxymethyl. R5=CH3 or CH3O. R6=H or CH3). (I) are intermediates for new macrolide antibiotics. New sugar residues or other substits. can be introduced easily without formation of an intramolecular cyclic acetal. In an example 6-(1,3-dioxolan-2-yl)methyl-3,5-dihydroxy-14-hydroxymethyl-4,8,12- -trimethyl-9-oxo-10,12-heptadecadien-15-olide was prepd. from the corresp. 5-(3,6-dideoxy-3-Me2N-beta-D-glucopyranosloxy) by reaction with m-Cl-perbenzoic acid and Ac2O.