SYNTHESIS AND BIOACTIVITY OF LINCOMYCIN-2-PHOSPHATE

Tritylation of 3,4‐O‐anisylidene lincomycin (II) was found to give 7‐O‐trityl‐3,4‐O‐anisplidene lincomycin (III), a key intermediate in the synthesis of lincomycin‐2‐monoesters. The structure of III was established by NMR. Phosphorylation of III with POCls in pyridine gave the resulting dichlorophosphate IV which after hydrolysis and treatment with 80% aqueous acetic acid (100°, 30 min.) gave lincomycin‐2‐phosphate (V). The water‐soluble ester V is inactive in the plate antibacterial assay using S. lutea, although in uiuo V is as active as the parent compound lincomycin (I) in mice infected with S. aureus. V gave slightly higher blood levels than the parent compound I upon oral administration in dogs. The taste of V is less bitter than I. Copyright © 1969 Wiley‐Liss, Inc., A Wiley Company