<i>N</i>-(<i>para</i>-Methoxyphenylpropargyl) Pyrrole-2-carboxylate (PPPC) Glycosides as Donors for Glycosylation
We developed glycosyl <i>N</i>-(<i>para</i>-methoxyphenylpropargyl) pyrrole-2-carboxylates (PPPCs) as highly effective donors for chemical glycosylation. The modular design and exceptional stability of the acid precursor provide PPPC donors with synthetic versatility and ease of use. Activated by NIS/TMSOTf, PPPC donors exhibit a broad compatibility for both <i>O</i>- and <i>N</i>-glycosylation reactions. Their distinct reactivity gradient enables streamlined one-pot syntheses, complementing thioglycosides and imidates. These features position PPPC donors as promising tools for advancing carbohydrate chemistry.
Authors
- Meifang Yang (ORCID: https://orcid.org/0000-0001-9899-3378)
- Yili Dai (ORCID: https://orcid.org/0000-0002-8307-6726)
- Houchao Tao (ORCID: https://orcid.org/0000-0001-7598-0275)
- Yitian Zhao (ORCID: https://orcid.org/0000-0003-4357-4592)
- Jingyu Tian
- Y. L. Qiu (ORCID: https://orcid.org/0000-0003-0524-1762)
- Song Li (ORCID: https://orcid.org/0000-0002-6427-3986)
- Xing Zheng (ORCID: https://orcid.org/0000-0001-5456-1143)
- Mengyu Li (ORCID: https://orcid.org/0000-0001-5020-8676)
- Xu Yao (ORCID: https://orcid.org/0009-0000-4984-4069)
Institutions
- Shanghai Innovative Research Center of Traditional Chinese Medicine (CN)
- Shanghai University of Traditional Chinese Medicine (CN)
- Hunan Vocational Institute of Technology (CN)
- Zhejiang Pharmaceutical College (CN)
- Hengyang Academy of Agricultural Sciences (CN)
- University of South China (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-12-25
- DOI
- https://doi.org/10.1021/acs.orglett.4c04389
- Citations
- 2
- Primary Topic
- Carbohydrate Chemistry and Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 0.50
Funders
- National Natural Science Foundation of China