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Synthesis
DOI: 10.1055/a-2502-7759
DOI: 10.1055/a-2502-7759
short review
Stereoselective Construction of Glycosides Enabled by Glycosyl/ Glycal Metal Species
The authors are grateful to the National Natural Science Foundation of China (22101250 and 22371247), the Yunnan Fundamental Research Projects (202301AW070005), the Yunnan Revitalization Talent Support Program (XDYC-QNRC-2022-0696), the Project of Innovative Research Team of Yunnan Province (202405AS350010), and the Yunnan University Research Innovation Fund for Graduate Students (KC-24249408) for financial support.
Abstract
Glycosyl/glycal metal functionalization has emerged as an efficient protocol for the construction of glycosides. Benefitting from the rapid development of organometallic chemistry and transition-metal-catalyzed cross-coupling reactions, glycosyl-metal-mediated glycosylation has significantly expanded the space for glycoside synthesis recently. In this short review, we underscore the representative progress in this area, categorizing the advancements by the type of glycosyl/glycal metal species. The reaction mechanism, stereochemical control, synthetic utility, and unmet challenges are also discussed.
1 Introduction
2 Glycosyl/Glycal Lithium-Based Glycosylations
2.1 Preparation of Glycosyl/Glycal Lithium Reagents
2.2 Glycosylation with Glycosyl/Glycal Lithiums
3 Glycosyl/Glycal Stannane-Based Glycosylations
3.1 Preparation of Glycosyl/Glycal Stannane Reagents
3.2 Glycosylation with Glycosyl/Glycal Stannanes
4 Glycosyl/Glycal Boron-Based Glycosylations
4.1 Preparation of Glycosyl/Glycal Boron Compounds
4.2 Glycosylation with Glycosyl/Glycal Boron Compounds
5 Glycosylations Enabled by in situ Formed Glycosyl-Metal Intermediates
5.1 Hydrofunctionalization of Glycals
5.2 Functionalization/Glycosylation of Glycals
6 Conclusion and Outlook
Key words
glycosides - stereoselective glycosylation - glycosyl-metal species - cross-coupling - functionalization - carbohydrate chemistryPublication History
Received: 22 November 2024
Accepted after revision: 15 December 2024
Accepted Manuscript online:
15 December 2024
Article published online:
23 January 2025
© 2025. Thieme. All rights reserved
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