2,2-Dichloro-1,3-benzodioxole as a Hydroxyl Protection Reagent for Carbohydrate Compounds
Changsheng Chen1, Shuang Li1, Henan Zhang1
1National Glycoengineering Research Center and Shandong Key Laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University, Qingdao 266237, People's Republic of China.
Abstract:
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.
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