Abstract
A facile synthesis of cellobiosan hexaacetate (II) was described. Zemplen degradation of II, followed by the Koenigs-Knorr reaction was shown to yield 1, 2, 3, 2', 3', 4', 6'-hepta-Oacetyl-β-cellobiose (III) in 45% yield. Crystalline 6-methylsulfonate (IV), p-tolylsulfonate (V), and 6-deoxy-6-iodo acetate (VI) were synthesized. Starting from IV, via the crystalline ethylxanthate (VIII), 1, 6-anhydro-6-thio-β-cellobiose (6-thiocellobiosan) (XIII) and the fully acetate (XII) were synthesized. Five fully acetylated cellobiose derivatives (VII, IX, X, XI, and XIV) having sulfur atom at C1, C6, or both of the positions were also synthesized starting from octaacetyl-β-cellobiose, IV, or XII.
