Selective N‐Deacetylation and Functionalization of Aminosugars

N‐Acetyl groups are abundant functional groups found in a variety of biomolecules including aminosugars. N‐Acetyl groups are chemically stable and harsh conditions are often needed to remove them. Herein, we report a mild and efficient protocol to remove N‐acetyl groups in the presence of esters and...

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Bibliographic Details
Published inEuropean journal of organic chemistry Vol. 2022; no. 31
Main Authors Moons, Sam J., Robertson, Alexander D., Boltje, Thomas J.
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 19.08.2022
Wiley Subscription Services, Inc
Subjects
Acylation
Aminoglycoside
Biomolecules
Carbamates (tradename)
Carbohydrates
Chemistry
Chemistry, Organic
Chemoselectivity
Esters
Functional groups
N-Deacetylation
Physical Sciences
Science & Technology
ELECTROPHILIC ACTIVATION
Carbohydrates
Chemoselectivity
Aminoglycoside
SECONDARY
SIALIC-ACID
GLYCOSYLATION
N-Deacetylation
Acylation
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Summary:N‐Acetyl groups are abundant functional groups found in a variety of biomolecules including aminosugars. N‐Acetyl groups are chemically stable and harsh conditions are often needed to remove them. Herein, we report a mild and efficient protocol to remove N‐acetyl groups in the presence of esters and carbamates and functionalize the resulting amine in a one‐pot manner. A mild and efficient one‐pot protocol to selectively remove N‐acetyl groups, and subsequently functionalize the generated amines, is reported. Common functional groups, such as esters, carbamates and thioglycosides, are tolerated.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202200659