2,2-Dichloro-1,3-benzodioxoleas a Hydroxyl ProtectionReagent for Carbohydrate Compounds

The application of 2,2-dichloro-1,3-benzodioxole (DCBZ) as a versatile hydroxyl protection reagent in carbohydrate chemistry has been demonstrated. DCBZ exhibited high reactivity with diverse vicinal and remote dihydroxyl groups in furanoses and pyranoses to form benzodioxole (BZDO)-protected products. The BZDO group showed remarkable stability under basic, redox, and glycosylation conditions and can be efficiently removed under acid conditions in the presence of a diol, highlighting its utility in the orthogonal synthesis of complex glycans.