Gram-Scale Synthesis\nof the Fucose-Containing Fragments\nof Saccharomicins

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

Publication Details

Journal
Figshare
Published
2024-10-17
DOI
https://doi.org/10.1021/acs.orglett.4c03599.s001
Primary Topic
Carbohydrate Chemistry and Synthesis
Type
article
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article

Gram-Scale Synthesis\nof the Fucose-Containing Fragments\nof Saccharomicins

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Carbohydrate Chemistry and Synthesis
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Gram-Scale Synthesis\nof the Fucose-Containing Fragments\nof Saccharomicins

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Abstract

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

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Carbohydrate Chemistry and Synthesis
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Gram-Scale Synthesis\nof the Fucose-Containing Fragments\nof Saccharomicins · Figshare (2024) | TGRS Research Map | TGRS