Hafnium(IV) triflate as a potent catalyst for selective 1-O-deacetylation of peracetylated saccharides

Rui Wang; Ji-Zong Chen; Xiu-An Zheng; Rui Kong; Shan-Shan Gong; Qi Sun

doi:10.1016/j.carres.2017.11.015

Hafnium(IV) triflate as a potent catalyst for selective 1-O-deacetylation of peracetylated saccharides

Carbohydr Res. 2018 Jan 2:455:114-118. doi: 10.1016/j.carres.2017.11.015. Epub 2017 Dec 5.

Authors

Rui Wang¹, Ji-Zong Chen¹, Xiu-An Zheng¹, Rui Kong¹, Shan-Shan Gong¹, Qi Sun²

Affiliations

¹ Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, 605 Fenglin Avenue, Nanchang, Jiangxi 330013, PR China.
² Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, 605 Fenglin Avenue, Nanchang, Jiangxi 330013, PR China. Electronic address: sunqi@jxstnu.edu.cn.

PMID: 29207316
DOI: 10.1016/j.carres.2017.11.015

Abstract

An efficient method for selective anomeric deacetylation of peracetylated mono-, di-, and trisaccharides has been developed by using 2 mol% Hf(OTf)₄ as catalyst in acetonitrile. Employment of ultrasonic irradiation could significantly accelerate the reaction rate. Mechanistic study confirmed the hydrolysis nature of this reaction, and NMR experimental data suggested that multiple peracetylated saccharide molecules may ligate to Hf(IV) cation primarily via the anomeric acetate to promote its specific hydrolysis.

Keywords: Deacetylation; Hafnium triflate; Peracetylated saccharides; Regioselectivity; Ultrasound.

MeSH terms

Catalysis
Hafnium / chemistry*
Molecular Structure
Oligosaccharides / chemistry*

Substances

Oligosaccharides
Hafnium