The deoxygenation of some carbohydrate diols via the derived cyclic thiocarbonate

JJ Patroni, RV Stick, LM Engelhardt, AH White

Index: Patroni, Joseph J.; Stick, Robert V.; Engelhardt, Lutz M.; White, Allan H. Australian Journal of Chemistry, 1986 , vol. 39, # 4 p. 699 - 711

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Citation Number: 10

Abstract

Abstract The treatment of methyl 2, 6-di-O-methyl-3, 4-O-thiocarbonyl-β-D-galactoside with methyl iodide gives mainly the 3-deoxy-3-iodo-D-guloside, whereas the α-anomer of the above and methyl 2-O-methyl-3, 4-O-thiocarbonyl-β-L-arabinoside give mainly the 4-deoxy- 4-iodo-D-glycosides. An explanation is given for these and some previously reported results. As well, two of the above cyclic thiocarbonates (β-D-galacto and β-L-arabino), together ...