Gram-Scale Synthesis of the Fucose-Containing Fragments of Saccharomicins

A highly efficient synthetic route has been established for the gram-scale production of fucose-aglycon (Fuc-Agl) and fucose-saccharosamine (Fuc-Sac) fragments in saccharomicins A and B. The β-glycosidic bonds within these structural components were formed through successive rhodium(II) and Brønsted-acid-catalyzed glycosylation, utilizing a stable thioglycosyl donor. Subsequent steps involving the installation of protecting groups yielded highly functionalized synthetic fragments that are suitable for further assembly of saccharomicins.

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Publication Details

Journal
Organic Letters
Published
2024-10-17
DOI
https://doi.org/10.1021/acs.orglett.4c03599
Citations
2
Primary Topic
Carbohydrate Chemistry and Synthesis
Type
article
Field-Weighted Citation Impact
0.50

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article

Gram-Scale Synthesis of the Fucose-Containing Fragments of Saccharomicins

Jing Zeng, Qian Wan, Shiwei Xu, Dengxian Fu et al.
2 citations
Organic Letters
Carbohydrate Chemistry and Synthesis
0.50
article

Gram-Scale Synthesis of the Fucose-Containing Fragments of Saccharomicins

Jing Zeng, Qian Wan, Shiwei Xu, Dengxian Fu, Ting Li, Lingkui Meng
article en
2 citations

Abstract

A highly efficient synthetic route has been established for the gram-scale production of fucose-aglycon (Fuc-Agl) and fucose-saccharosamine (Fuc-Sac) fragments in saccharomicins A and B. The β-glycosidic bonds within these structural components were formed through successive rhodium(II) and Brønsted-acid-catalyzed glycosylation, utilizing a stable thioglycosyl donor. Subsequent steps involving the installation of protecting groups yielded highly functionalized synthetic fragments that are suitable for further assembly of saccharomicins.

Organic LettersVol. 26(43)
Wuhan University (CN), Huazhong University of Science and Technology (CN)
National Natural Science Foundation of China, National Key Research and Development Program of China
Zero hunger
Openalex Percentile: Top 38%
Carbohydrate Chemistry and Synthesis
0.50
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Gram-Scale Synthesis of the Fucose-Containing Fragments of Saccharomicins — Jing Zeng, Qian Wan, et al. · Organic Letters (2024) | TGRS Research Map | TGRS