A Novel and Efficient Deprotection of the Allyl Group at the Anomeric Oxygen of Carbohydrates

Biao Yu; Jianbo Zhang; Shoufu Lu; Yongzheng Hui

doi:10.1055/s-1998-1579

Synlett 1998; 1998(1): 29-30
DOI: 10.1055/s-1998-1579

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A Novel and Efficient Deprotection of the Allyl Group at the Anomeric Oxygen of Carbohydrates

Biao Yu^* , Jianbo Zhang, Shoufu Lu, Yongzheng Hui

^*State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China; Fax 21 64 16 61 28; E-mail: byusioc@fudan.ac.cn

Abstract

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Perfluoroalkylation with perfluoroalkyl iodide under sodium dithionite and sodium bicarbonate in acetonitrile/water followed by elimination in the presence of zinc powder and ammonium chloride in ethanol was disclosed to be an extremely mild and efficient procedure for deprotection of the anomeric allyl group of carbohydrates.

deallylation - allyl glycoside - perfluoroalkylation

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