Photocatalytic Synthesisof Difluorinated GlycoaminoAcids and Neoglycopeptides via Hydrodifluoroacetamidation of Vinyl-C-glycosides

A photocatalytic approach for the synthesis of difluorinated glycoamino acids and neoglycopeptides from bromodifluoroacetamides and sugar-derived olefins is presented. This method stands out because of its simplicity, atomic economy, and mild reaction conditions, allowing compatibility with both natural and unnatural amino acids and peptides. Additionally, it demonstrates efficacy across a variety of carbohydrates, including furanoses, pyranoses, pentose, hexoses, and disaccharides, accommodating an extensive range of protecting groups, even in their deprotected forms.

Publication Details

Journal
Figshare
Published
2025-03-04
DOI
https://doi.org/10.1021/acs.joc.5c00030.s001
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.00
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article

Photocatalytic Synthesisof Difluorinated GlycoaminoAcids and Neoglycopeptides via Hydrodifluoroacetamidation of Vinyl-C-glycosides

Figshare
Fluorine in Organic Chemistry
article

Photocatalytic Synthesisof Difluorinated GlycoaminoAcids and Neoglycopeptides via Hydrodifluoroacetamidation of Vinyl-C-glycosides

article en

Abstract

A photocatalytic approach for the synthesis of difluorinated glycoamino acids and neoglycopeptides from bromodifluoroacetamides and sugar-derived olefins is presented. This method stands out because of its simplicity, atomic economy, and mild reaction conditions, allowing compatibility with both natural and unnatural amino acids and peptides. Additionally, it demonstrates efficacy across a variety of carbohydrates, including furanoses, pyranoses, pentose, hexoses, and disaccharides, accommodating an extensive range of protecting groups, even in their deprotected forms.

Figshare
Openalex Percentile: Top 60%
Fluorine in Organic Chemistry
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Photocatalytic Synthesisof Difluorinated GlycoaminoAcids and Neoglycopeptides via Hydrodifluoroacetamidation of Vinyl-C-glycosides · Figshare (2025) | TGRS Research Map | TGRS