Nitrogen-containing Sugars. V. Synthesis and Deamination of Methyl 4, 6-Benzylidene-β-D-glucosaminide Hydrochloride.

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Abstract
Methyl 4, 6-benzylidene-β-D-glucosaminide hydrochloride (III) was synthesized by a new method. Deamination of (III) with sodium nitrite in weak acetic acidity resulted in facile cleavage of glycosidic bond and simultaneous dehydration between C-2 and C-5 positions to form 2, 5-anhydro-4, 6-benzylidene-D-mannose. On the other hand, deamination of methyl 2-amino-4, 6-benzylidene-2-desoxy-α-D-altroside hydrochloride (V) with sodium nitrite afforded methyl 2, 3-anhydro-4, 6-benzylidene-α-D-alloside (VI) without any change in glycosidic bond. The mechanisms of these deamination reactions were discussed.

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