Development\nof Glycosylation Protocols Using Glycosyl <i>N</i>‑Phenylethynyl\nPyrrole-2-carboxylates as Donors

We herein introduce glycosyl <i>N</i>-phenylethynyl\npyrrole-2-carboxylates\n(PEPCs) as novel and highly efficient glycosyl donors. The unique\ninclusion of the pyrrole group, serving as both an electron-donating\ngroup and an <i>ortho</i>-tethering scaffold, imparts exceptional\nshelf stability while retaining reactivity for glycosylation reactions.\nPEPC donors exhibit broad utility for both <i>O</i>- and <i>N</i>-glycosylation across a variety of substrates. Additionally,\ntheir versatility and efficiency were further demonstrated in a one-pot\nsaccharide synthesis, showcasing their potential for diverse synthetic\napplications.

Publication Details

Journal
Figshare
Published
2024-11-12
DOI
https://doi.org/10.1021/acs.orglett.4c03768.s001
Primary Topic
Mycorrhizal Fungi and Plant Interactions
Type
article
Field-Weighted Citation Impact
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article

Development\nof Glycosylation Protocols Using Glycosyl N‑Phenylethynyl\nPyrrole-2-carboxylates as Donors

Figshare
Mycorrhizal Fungi and Plant Interactions
article

Development\nof Glycosylation Protocols Using Glycosyl N‑Phenylethynyl\nPyrrole-2-carboxylates as Donors

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Abstract

We herein introduce glycosyl <i>N</i>-phenylethynyl\npyrrole-2-carboxylates\n(PEPCs) as novel and highly efficient glycosyl donors. The unique\ninclusion of the pyrrole group, serving as both an electron-donating\ngroup and an <i>ortho</i>-tethering scaffold, imparts exceptional\nshelf stability while retaining reactivity for glycosylation reactions.\nPEPC donors exhibit broad utility for both <i>O</i>- and <i>N</i>-glycosylation across a variety of substrates. Additionally,\ntheir versatility and efficiency were further demonstrated in a one-pot\nsaccharide synthesis, showcasing their potential for diverse synthetic\napplications.

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Mycorrhizal Fungi and Plant Interactions
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Development\nof Glycosylation Protocols Using Glycosyl <i>N</i>‑Phenylethynyl\nPyrrole-2-carboxylates as Donors · Figshare (2024) | TGRS Research Map | TGRS