Some diphenylphosphorus(V) group monosaccharide compounds derived from methyl 2,3-O-isopropylidene-α-D-mannofuranoside

Abstract

Methyl 6-O-diphenylphosphinoyl-2,3-O-isopropylidene-α-D-mannofuranoside 2 is obtained by aerial oxidation of the product of the reaction of methyl 2,3-O-isopropylidene-α-D-mannofuranoside 1 and Ph₂PCI in the presence of a base. Methyl 2,3-O-isopropylidene-5,6-bis-O-methylsulfonyl-α-D-mannofuranoside 4; R = Me reacts with Ph₂PLi to give, after aerial oxidation, methyl 6-deoxy-6-C-diphenylphosphinoyl-2,3-O-isopropylidene-5-O-methylsulfonyl-α-D-mannofuranoside 5 and methyl 6-deoxy-6-C-diphenylphosphinoyl-2,3-O-isopropylidene-β-L-gulofuranoside 6. Also prepared are the 5-O-toluene p-sulfonyl analogue of compound 2 and 2,3 : 5,6-bis-O-isopropylidene-1-O-diphenylphosphinoyl-α-D-mannofuranoside 8. Crystal structures of compounds 4; (R = Me) and 2 are determined: the furanose ring in both compounds is in a °E conformation. Intermolecular H-bonding, involving the PO and OH groups, links the molecules of compound 2 into chains.