THE BROMINOLYSIS OF CARBOHYDRATE IODIDES: II. A SYNTHETIC ROUTE TO 2,5-ANHYDROSUGARS

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Abstract
Reaction of methyl 2-deoxy-2-iodo-β-D-glucopyranoside triacetate with a 20-fold excess of bromine and a 10-fold excess of silver acetate in a 10% solution of potassium acetate in acetic acid gave a near-quantitative yield of an equimolar mixture of the anomeric forms of 1,3,4,6-tetra-O-acetyl-2,5-anhydro-1-methoxy-D-mannose. Treatment of the mixture with methanolic hydrogen chloride gave the dimethylacetal of 2,5-anhydro-D-mannose (chitose).

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