Glycosylation Enabled by Successive Rhodium(II) and Brønsted Acid Catalysis.


Journal

Journal of the American Chemical Society
ISSN: 1520-5126
Titre abrégé: J Am Chem Soc
Pays: United States
ID NLM: 7503056

Informations de publication

Date de publication:
31 07 2019
Historique:
pubmed: 18 7 2019
medline: 18 7 2019
entrez: 18 7 2019
Statut: ppublish

Résumé

Herein, we reported on a highly efficient glycosylation reaction comprising two chronological meticulously designed catalytic cycles: (1) rhodium-catalyzed formation of sulfonium ylide and (2) Brønsted acid-catalyzed formation of sulfonium ion. This protocol highlighted an effective and robust tactic to prepare a glycosyl sulfonium ion from a glycosyl sulfonium ylide precursor amenable for glycosylation.

Identifiants

pubmed: 31314513
doi: 10.1021/jacs.9b04619
doi:

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

11775-11780

Auteurs

Lingkui Meng (L)

Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy , Huazhong University of Science and Technology , 13 Hangkong Road , Wuhan , Hubei 430030 , China.

Peng Wu (P)

Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy , Huazhong University of Science and Technology , 13 Hangkong Road , Wuhan , Hubei 430030 , China.

Jing Fang (J)

Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy , Huazhong University of Science and Technology , 13 Hangkong Road , Wuhan , Hubei 430030 , China.

Ying Xiao (Y)

Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy , Huazhong University of Science and Technology , 13 Hangkong Road , Wuhan , Hubei 430030 , China.

Xiong Xiao (X)

Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy , Huazhong University of Science and Technology , 13 Hangkong Road , Wuhan , Hubei 430030 , China.

Guangsheng Tu (G)

Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy , Huazhong University of Science and Technology , 13 Hangkong Road , Wuhan , Hubei 430030 , China.

Xiang Ma (X)

Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy , Huazhong University of Science and Technology , 13 Hangkong Road , Wuhan , Hubei 430030 , China.

Shuang Teng (S)

Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy , Huazhong University of Science and Technology , 13 Hangkong Road , Wuhan , Hubei 430030 , China.

Jing Zeng (J)

Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy , Huazhong University of Science and Technology , 13 Hangkong Road , Wuhan , Hubei 430030 , China.

Qian Wan (Q)

Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy , Huazhong University of Science and Technology , 13 Hangkong Road , Wuhan , Hubei 430030 , China.

Classifications MeSH