The synthesis of methyl 2-O-benzoyl-3,4-O-(S)- and methyl 2-O-benzoyl-3,4-O-(R)-benzylidene-β-L-ribopyranoside
Benzylidenation of methyl β-L-arabinopyranoside, by the method of Oldham and Honeyman, followed by benzoylation, gave methyl 2-O-benzoyl-3,4-O-(S)-benzylidene-β-L-arabinopyranoside (1). Selective acid hydrolysis of a 1:1 mixture of the diastereomeric forms of methyl 2-O-benzoyl-3,4-O-benzylidene-β-L-arabinopyranoside gave the (R)-isomer (3). Debenzoylation of 1 and 3 gave methyl 3,4-O-(S)-and methyl 3,4-O-(R)-benzylidene-β-L-arabinopyranoside (2 and 4) respectively. Oxidation of 2, followed by reduction and benzoylation, gave methyl 2-O-benzoyl-3,4-O-(S)-benzylidene-β-L-ribopyranoside (7). A similar reaction sequence with 4 gave methyl 2-O-benzoyl-3,4-O-(R)-benzylidene-β-L-ribopyranoside (8).