J. S. Brimacombe, O. A. Ching
1969
Citations
0
Influential Citations
3
Citations
Journal
Journal of The Chemical Society C: Organic
Abstract
Solvolysis of benzyl 5-O-p-bromophenylsulphonyl-2,3-O-isopropylidene-β-D-ribofuranoside (1) in 50% aqueous methanol-sodium acetate yielded principally benzyl 2,3-O-isopropylidene-β-D-ribofuranoside (2), benzyl 2,3-O-isopropylidene-5-O-methyl-β-D-ribofuranoside (3), 5-O-benzyl-2,3-O-isopropylidene-β-D-ribofuranose (4), and methyl 5-O-benzyl-2,3-O-isopropylidene-β-D-ribofuranoside (5). Compounds (2) and (3) arise by direct solvolytic displacement of the sulphonic ester group while the rearranged products (4) and (5) are formed as a consequence of benzyloxy-group participation in the displacement of the sulphonic ester group.