Regioselective Anomeric O‐Benzyl Deprotection in Carbohydrates

A highly regioselective hydrogenolysis of the anomeric benzyl group is reported. The reaction involves selective acetolysis of benzyl acetals of various mono‐ and di‐saccharides using 10 % Pd/C under hydrogen atmosphere in the presence of Na2CO3. The generality of the methodology is evaluated by app...

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Bibliographic Details
Published in:European journal of organic chemistry 2021-11, Vol.2021 (41), p.5665-5668
Main Authors: Sridhar, Perali Ramu, Anjaneyulu, Bandi, Rao, Boddu Umamaheswara
Format: Article
Language:English
Subjects:
Acetals
Carbohydrates
Glycosides
Hemiacetals
Hydrogenolysis
Protecting groups
Regioselectivity
Sodium carbonate
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Summary:A highly regioselective hydrogenolysis of the anomeric benzyl group is reported. The reaction involves selective acetolysis of benzyl acetals of various mono‐ and di‐saccharides using 10 % Pd/C under hydrogen atmosphere in the presence of Na2CO3. The generality of the methodology is evaluated by applying it to a number of perbenzylated/orthogonally protected benzyl glycosides. A simple and highly regioselective hydrogenolysis of the anomeric benzyl group is reported. The generality and the scope of the reaction were evaluated by applying it to a number of diversly protected benzyl monosaccharides and disaccharides that lead to the formation of the corresponding hemiacetals in good yield.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202101033