SYNTHESIS AND CONFORMATIONS OF 2,3:4,5- AND 2,4:3,5-DI-O-ISOPROPYLIDENE-D-MANNITOL

Article abstract of DOI:10.1016/0008-6215(88)84059-X

The 2,3:4,5- (8) and 2,4:3,5-di-O-isopropylidene (10) derivatives of D-mannitol have been prepared from 1,6-di-O-benzoyl-D-mannitol and their structures established by (13)C-n.m.r. spectroscopy.The 1,3-dioxane rings in 10 adopt a skew conformation and the sugar carbon chain in 8 is bent around the C-3-C-4 bond, as found by i.r. data and molecular mechanics calculations.Oxidation of 8 with pyridinium dichromate gave 2,3:4,5-di-O-isopropylidene-D-mannono-1,6-lactone (12).