Abstract:
Penta-O-acetyl-D-glucose diethyl dithioacetal monoxide 3 was obtained by oxidation of
penta-O-acetyl-D-glucose diethyl dithioacetal 2 with 3-chloroperbenzoic acid. By reaction of 3 with sodium methoxide in methanol and further acetylation, 3,4,6-tri-O-acetyl-2,5-anhydro-D-mannose-diethyl dithioacetal monoxide 8 and the reduction product 3,4,6-tri-O-acetyl-2,5-anhydro-1,1-bis(ethylthio)-1-deoxy-D-arabino-
-hex-1-enitol 4 were obtained. Reduction of 8 yielded the correponding dithioacetal derivative 9, which was converted to 3,4,6-O-acetyl-2,5-anhydro-D-mannose diethyl acetal 11.