Synthesis of ether-linked sugar by nucleophilic opening of carbohydrate oxiranes.

[摘要]：A new synthesis of ether-linked sugars utilizing the nucleophilic ring-opening of carbohydrate a- or b-oxirane was developed. The reaction of 2,3-anhydro-a-D-mannopyranosides resulted in the expected high regioselectivity. In contrast, 2,3-anhydro-a-D-allopyranosides showed an unusual regioselectivity shift. The differentiating properties of carbohydrate a- or b-oxirane were investigated by comparing various conditions of the reaction.

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