<i>N</i>‑(<i>para</i>-Methoxyphenylpropargyl)\nPyrrole-2-carboxylate (PPPC) Glycosides as Donors for Glycosylation

We\ndeveloped glycosyl <i>N</i>-(<i>para</i>-methoxyphenylpropargyl)\npyrrole-2-carboxylates (PPPCs) as highly\neffective donors for chemical glycosylation. The modular design and\nexceptional stability of the acid precursor provide PPPC donors with\nsynthetic versatility and ease of use. Activated by NIS/TMSOTf, PPPC\ndonors exhibit a broad compatibility for both <i>O</i>-\nand <i>N</i>-glycosylation reactions. Their distinct reactivity\ngradient enables streamlined one-pot syntheses, complementing thioglycosides\nand imidates. These features position PPPC donors as promising tools\nfor advancing carbohydrate chemistry.

Publication Details

Journal
Figshare
Published
2024-12-25
DOI
https://doi.org/10.1021/acs.orglett.4c04389.s001
Primary Topic
Carbohydrate Chemistry and Synthesis
Type
article
Field-Weighted Citation Impact
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article

N‑(para-Methoxyphenylpropargyl)\nPyrrole-2-carboxylate (PPPC) Glycosides as Donors for Glycosylation

Figshare
Carbohydrate Chemistry and Synthesis
article

N‑(para-Methoxyphenylpropargyl)\nPyrrole-2-carboxylate (PPPC) Glycosides as Donors for Glycosylation

article en

Abstract

We\ndeveloped glycosyl <i>N</i>-(<i>para</i>-methoxyphenylpropargyl)\npyrrole-2-carboxylates (PPPCs) as highly\neffective donors for chemical glycosylation. The modular design and\nexceptional stability of the acid precursor provide PPPC donors with\nsynthetic versatility and ease of use. Activated by NIS/TMSOTf, PPPC\ndonors exhibit a broad compatibility for both <i>O</i>-\nand <i>N</i>-glycosylation reactions. Their distinct reactivity\ngradient enables streamlined one-pot syntheses, complementing thioglycosides\nand imidates. These features position PPPC donors as promising tools\nfor advancing carbohydrate chemistry.

Figshare
Openalex Percentile: Top 79%
Carbohydrate Chemistry and Synthesis
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<i>N</i>‑(<i>para</i>-Methoxyphenylpropargyl)\nPyrrole-2-carboxylate (PPPC) Glycosides as Donors for Glycosylation · Figshare (2024) | TGRS Research Map | TGRS