Studies on the synthesis of methyl 2,3-anhydro-4,6-O-benzylidene-β-D-allopyranoside and -mannopyranoside, and their reaction with sodium azide

Selective Benzoylation of Methyl 6-Deoxy-α- and β-D-glucopyranosides

“…the 2-OH group while the reverse is true for the u-anon~er. The high reactivity of the 2-OH group in the cr-anomer may be due to intramolecular hydrogen bonding between the 2-OH group and the axial C-1 ~nethoxyl group (8,9,13,14), and the lower reactivity of the 2-OH group in the P-anomer may be attributed to lack of hydrogen bond formation (13,15,16). It is of interest to note that the 4-OH group in methyl 6-deoxy-uand P-D-glucopyranosides is the least reactive towards benzoylation while it is more reactive than the other secondary hydroxyl groups in selective disulfonylation of methyl 0-D-glucopyranoside (1 7).…”

Monomolar Etherification of Methyl 4, 6-O-Benzylidene-α- and β-d-Glucopyranosides

“…BioI. Chem., 39 (9), 1879~ 1881,1975 oxide and barium hydroxide. After stirring for 20 hr at room temperature, the reaction mixture was chromatographed on silicic acid to yield four fractions: methyl 2,3 -di -0 -benzyl-4,6 -0 -benzy Iidene-a-D-glucopyranoside (11 %), the 2-0-benzyl ether (11 %), the 3-0-benzyl ether (3 %) and the starting material I (30%).…”