Ring opening reactions of benzyl 3,4-anhydro-β-D-ribopyranoside with nucleophiles

Article abstract of DOI:10.1016/0040-4020(95)01010-6

By the proper choice of metal counterion it is possible to regioselectively cleave with a variety of nucleophiles, the epoxide ring of benzyl 3, 4-anhydro-β-D-ribopyranoside. The resulting 3-deoxy 3-substituted or 4-deoxy 4-substituted glycosides were obtained in good yields. Factors governing the regiochemistry of ring opening are discussed.