SOME DIPHENYLPHOSPHORUS(V) GROUP MONOSACCHARIDE COMPOUNDS DERIVED FROM METHYL 2,3-O-ISOPROPYLIDENE-ALPHA-D-MANNOFURANOSIDE

Methyl inoyl-2,3-O-isopropylidene-alpha-D-mannofuranoside 2 is obtaine d by aerial oxidation of the product of the reaction of methyl 2,3-O-i sopropylidene-alpha-D-mannofuranoside 1 and Ph(2)PCl in the presence o f a base, Methyl 2,3- e-5,6-bis-O-methylsulfonyl-alpha-D-mannofuranosi de 4; R = Me reacts with Ph(2)PLi to give, after aerial oxidation, met hyl noyl-2,3-O-isopropylidene-5-O-methylsulfonyl-alpha and methyl sphi noyl-2,3-O-isopropylidene-beta-L-glufuranoside 6. Also prepared are th e 5-O-toluene-p-sulfonyl analogue of compound 2 and ne-1-O-diphenylpho sphinoyl-alpha-D-mannofuranoside 8. Crystal structures of compounds 4; (R = Me) and 2 are determined: the furanose ring in both compounds is in a degrees E conformation. Intermolecular H-bonding, involving the P=O and OH groups, links the molecules of compound 2 into chains.