Issue 5, 2016
From the journal:

Organic & Biomolecular Chemistry

Stereoselective synthesis of β-rhamnopyranosides via gold(i)-catalyzed glycosylation with 2-alkynyl-4-nitro-benzoate donors†

Yugen Zhu,‡a   Zhengnan Shen,‡b   Wei Lia  and  Biao Yu*a  

* Corresponding authors

a State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China
E-mail: byu@mail.sioc.ac.cn

b School of Physical Science and Technology, ShanghaiTech University, 100 Haike Road, Shanghai 201210, China

Abstract

Stereoselective β-rhamnopyranosylation remains a challenge, due to the unfavorable anomeric effect and steric hindrance of the C2-substituent; herein, this challenge is addressed with a gold(I)-catalyzed SN2-like glycosylation protocol employing α-rhamnopyranosyl 2-alkynyl-4-nitro-benzoates as donors.

Graphical abstract: Stereoselective synthesis of β-rhamnopyranosides via gold(i)-catalyzed glycosylation with 2-alkynyl-4-nitro-benzoate donors

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Article information

DOI
https://doi.org/10.1039/C5OB02551F
Article type
Communication
Submitted
17 Nov 2015
Accepted
15 Dec 2015
First published
15 Dec 2015

Org. Biomol. Chem., 2016,14, 1536-1539

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Stereoselective synthesis of β-rhamnopyranosides via gold(I)-catalyzed glycosylation with 2-alkynyl-4-nitro-benzoate donors

Y. Zhu, Z. Shen, W. Li and B. Yu, Org. Biomol. Chem., 2016, 14, 1536 DOI: 10.1039/C5OB02551F

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