Palladium-catalyzed Suzuki-Miyaura Cross-couplings of Stable Glycal Boronates for Robust Synthesis of C-1 Glycals

Overview

Journal Nat Commun

Specialty Biology

Date 2024 Jun 19

PMID 38898022

Authors

Anrong Chen

Yang Han

Rongfeng Wu

Bo Yang

Lijuan Zhu

Feng Zhu

Affiliations

Soon will be listed here.

Abstract

C-1 Glycals serve as pivotal intermediates in synthesizing diverse C-glycosyl compounds and natural products, necessitating the development of concise, efficient and user-friendly methods to obtain C-1 glycosides is essential. The Suzuki-Miyaura cross-coupling of glycal boronates is notable for its reliability and non-toxic nature, but glycal donor stability remains a challenge. Herein, we achieve a significant breakthrough by developing stable glycal boronates, effectively overcoming the stability issue in glycal-based Suzuki-Miyaura coupling. Leveraging the balanced reactivity and stability of our glycal boronates, we establish a robust palladium-catalyzed glycal-based Suzuki-Miyaura reaction, facilitating the formation of various C(sp)-C(sp), C(sp)-C(sp), and C(sp)-C(sp) bonds under mild conditions. Notably, we expand upon this achievement by developing the DNA-compatible glycal-based cross-coupling reaction to synthesize various glycal-DNA conjugates. With its excellent reaction reactivity, stability, generality, and ease of handling, the method holds promise for widespread appication in the preparation of C-glycosyl compounds and natural products.

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