SYNTHESIS OF CITRONELLYL AND DOLICHYL GLY COSYL PHOSPHATES AND BETA-D-GLUCOSE AND BETA-D-GALACTOSE DERIVATIVES BY THE H-PHOSPHONATE METHOD

The possibility of obtaining alpha-dihydropolyprenyl glycosyl phosphat es by the glycosyl H-phosphonate method was shown. For starting 2,3,4, 6-tetra-O-acetyl-beta-D-glucopyranosyl and -galactopyranosyl H-phospho nates, a method of synthesis was worked out based on the reaction of 1 ,2-orthoacetates of the corresponding carbohydrates with H3PO3. Intera ction of the glycosyl H-phosphonates with citronellol or dolichol, fol lowed by oxidation and removal of protective groups, yields citronelly l and dolichyl glycosyl phosphates, the derivatives of beta-D-glucose and beta-D-galactose.