Citation: Qingpeng Zhao, Shihao Zhou, Yue Wang, Xiaoyu Yang, Youhui Meng, Yanxin Zhang, Jian Gao. Stereoselective synthesis of the 3, 6-branched Fuzi α-glucans up to 15-mer via a one-pot and convergent glycosylation strategy[J]. Chinese Chemical Letters, ;2023, 34(6): 107982. doi: 10.1016/j.cclet.2022.107982 shu

Stereoselective synthesis of the 3, 6-branched Fuzi α-glucans up to 15-mer via a one-pot and convergent glycosylation strategy

Qingpeng Zhao ^{a, 1} ,
Shihao Zhou ^{a, 1} ,
Yue Wang ^{a, 1} ,
Xiaoyu Yang ^a ,
Youhui Meng ^a ,
Yanxin Zhang ^b ,
Jian Gao ^{a, *,}

a.
National Glycoengineering Research Center, Shandong Key Laboratory of Carbohydrate Chemistry and Glycobiology, NMPA Key Laboratory for Quality Research and Evaluation of Carbohydrate-based Medicine, Shandong University, Qingdao 266237, China
b.
Department of Pharmaceutical Engineering, College of Chemical Engineering, Northwest University, Xiʹan 710069, China

jgao@sdu.edu.cn

Received Date: 18 August 2022
Revised Date: 26 October 2022
Accepted Date: 3 November 2022
Available Online: 6 November 2022

Figures(6)

A family of the 3, 6-branched Fuzi α-glucans including the pentasaccharide repeating unit as well as its di- and trimers were efficiently achieved via a one-pot and convergent glycosylation strategy. All the protected α-glucans up to 15-mer were assembled with high yields and excellent α-stereoselectivity, which was secured by the synergistic α-directing effects of the TolSCl/AgOTf promotion system and the steric β-facial shielding of bulky saccharide residues linked at the 6-O-position of glucosyl donors. Moreover, the 3, 6-branched architecture of glycosyl donor was revealed to be more favorable for the α-selective glucosidation of primary hydroxyl group, especially in the case of large oligosaccharide acceptor. The structurally well-defined synthetic α-glucans would be useful for various biological studies.
- α-D-Glucan,
- One-pot synthesis,
- Convergent glycosylation,
- Stereoselective synthesis,
- Thioglycoside
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