One-pot carbanionic access to methylenebis(phosphonate) analogues of natural P1,P2-glycosyl-disubstituted pyrophosphates

Two novel lithiated carbanions derived from ethyl (1,2:3,4-diisopropylidene-alpha-D-galactopyranosyl) methyl phosphonate 3a and ethyl (1-O-methyl-2,3-O-isopropylidene-beta-D-ribofuranosyl) methylphosphonate 3b were used in the one-pot alkylidene diphosphorylation of 2,3-O-isopropylidene uridine or 2,3:5,6-di-O-isopropylidene-D-mannofuranose to synthesise the methylene-bis(phosphonate) analogues of natural P-1, P-2-glycosyl-disubstituted pyrophosphates. (c) 2005 Elsevier Ltd. All rights reserved.