Glycosyl Esters as Stable Donors in Chemical Glycosylation

Abstract Efficient glycosylation methods are continuously being developed to obtain homogeneously pure carbohydrates to study their biological roles. The development of effective and stereoselective glycosylations using novel anomeric leaving groups constitutes an active area of research in synthetic carbohydrate chemistry. Although various glycosyl donors have been developed over the decades, anomeric esters as donors in glycosylation have received significant attention in recent times due to their convenience of preparation, shelf stability, catalytic activation, mild conditions, and high glycosylation efficiency. We focus in this review on several synthetic strategies for the assembly of the glycosyl ester‐containing donors utilized in chemical glycosylation methods, including simple esters, alkenyl, alkynyl‐containing esters, carbonate esters, chelation‐assisted glycosyl esters, allenyl and ynenoate glycosyl esters in glycoside synthesis are summarized.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2024-12-30
DOI
https://doi.org/10.1002/ejoc.202401330
Citations
8
Primary Topic
Carbohydrate Chemistry and Synthesis
Type
article
Field-Weighted Citation Impact
2.00
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article

Glycosyl Esters as Stable Donors in Chemical Glycosylation

Someswara Sanapala, Sumit Pareek, Pavan Mandadi
8 citations
European Journal of Organic Chemistry
Carbohydrate Chemistry and Synthesis
2.00
article

Glycosyl Esters as Stable Donors in Chemical Glycosylation

Someswara Sanapala, Sumit Pareek, Pavan Mandadi
article en
8 citations

Abstract

Abstract Efficient glycosylation methods are continuously being developed to obtain homogeneously pure carbohydrates to study their biological roles. The development of effective and stereoselective glycosylations using novel anomeric leaving groups constitutes an active area of research in synthetic carbohydrate chemistry. Although various glycosyl donors have been developed over the decades, anomeric esters as donors in glycosylation have received significant attention in recent times due to their convenience of preparation, shelf stability, catalytic activation, mild conditions, and high glycosylation efficiency. We focus in this review on several synthetic strategies for the assembly of the glycosyl ester‐containing donors utilized in chemical glycosylation methods, including simple esters, alkenyl, alkynyl‐containing esters, carbonate esters, chelation‐assisted glycosyl esters, allenyl and ynenoate glycosyl esters in glycoside synthesis are summarized.

European Journal of Organic ChemistryVol. 28(10)
Indian Institute of Technology Tirupati (IN)
Openalex Percentile: Top 14%
Carbohydrate Chemistry and Synthesis
2.00
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