1,2-Tans-1-dihydroxyboryl benzyl S-glycoside as glycosyl donor

Xiao Liu; Bingbing Zhang; Xiangying Gu; Guohua Chen; Lin Chen; Xin Wang; Bing Xiong; Qi-Dong You; Yue-Lei Chen; Jingkang Shen

doi:10.1016/j.carres.2014.05.010

1,2-Tans-1-dihydroxyboryl benzyl S-glycoside as glycosyl donor

Carbohydr Res. 2014 Oct 29:398:45-9. doi: 10.1016/j.carres.2014.05.010. Epub 2014 May 22.

Authors

Xiao Liu¹, Bingbing Zhang², Xiangying Gu¹, Guohua Chen³, Lin Chen⁴, Xin Wang⁴, Bing Xiong⁴, Qi-Dong You⁵, Yue-Lei Chen⁶, Jingkang Shen⁷

Affiliations

¹ School of Pharmacy, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210009, PR China; Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, PR China.
² Sinochem Jiangsu Co, Ltd, 22F Jincheng Dasha, 216 Longpan Zhonglu, Baixia Qu, Nanjing 210002, PR China.
³ School of Pharmacy, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210009, PR China.
⁴ Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, PR China.
⁵ School of Pharmacy, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210009, PR China. Electronic address: [email protected].
⁶ Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, PR China. Electronic address: [email protected].
⁷ Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, PR China. Electronic address: [email protected].

PMID: 25240181
DOI: 10.1016/j.carres.2014.05.010

Abstract

Activated by NBS, readily available 1,2-trans-1-dihydroxyboryl benzyl S-glycosides served as glycosyl donors and reacted with certain simple alcohol acceptors to produce pure 1,2-cis-O-glycosides in moderate yields. The boronic acid moiety was revealed essential in the glycosylation for product formation and good anomeric ratio. The preliminary model reactions suggested that glycosyl aryl boronic acids could be used for stereoselective glycosylation.

Keywords: Ate complex; Boronic acid; Glycosylation; S-Glycoside; Stereoselective.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Boronic Acids / chemistry*
Glycosides / chemistry*
Glycosylation
Stereoisomerism
Substrate Specificity

Substances

Boronic Acids
Glycosides