Citation: Ao Sun, Zipeng Li, Shuchun Li, Xiangbao Meng, Zhongtang Li, Zhongjun Li. Stereoselective synthesis of α-3-deoxy-D-manno-oct-2-ulosonic acid (α-Kdo) derivatives using a C3-p-tolylthio-substituted Kdo fluoride donor[J]. Chinese Chemical Letters, ;2025, 36(3): 109972. doi: 10.1016/j.cclet.2024.109972 shu

Stereoselective synthesis of α-3-deoxy-D-manno-oct-2-ulosonic acid (α-Kdo) derivatives using a C3-p-tolylthio-substituted Kdo fluoride donor

Ao Sun ^a ,
Zipeng Li ^a ,
Shuchun Li ^a ,
Xiangbao Meng ^a ,
Zhongtang Li ^a ,
Zhongjun Li ^{a, b, *,}

a.
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China
b.
Ningbo Institute of Marine Medicine, Peking University, Ningbo 315832, China

zjli@bjmu.edu.cn

Received Date: 7 February 2024
Revised Date: 22 April 2024
Accepted Date: 7 May 2024
Available Online: 8 May 2024

Figures(6)

3-Deoxy-D-manno-oct-2-ulosonic acid (Kdo) is widely distributed in bacteria, and the synthesis of Kdo-containing oligosaccharides is important for the development of novel antibiotics and immunological agents. We have recently developed a strategy to achieve α-stereocontrolled glycosylation using a C3-p-tolylthio-substituted Kdo phosphite donor. The wide substrate scope and high reactivity of the donors enabled the efficient synthesis of a series of Kdo-containing glycosides with complete α-stereoselectivity and without the formation of 2,3-ene byproducts. In this study, we improved the method by replacing the leaving group diethyl phosphite with fluoride, which enhanced the stability of the donor and led to cleaner reaction. Furthermore, the substrate range was expanded by synthesizing a series of Kdo O/C/S/N-glycosides, which also opened up a new avenue for the synthesis of CMP-Kdo synthase inhibitors.
- Glycosylation,
- Kdo glycosides,
- Stereoselectivity,
- Synthetic method,
- Glycoderivatives
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