Improved Synthesis of 1-O-Acyl-β-d-Glucopyranose Tetraacetates

Yu Chen; Huan Lu; Yanyu Chen; Wansheng Yu; Hui Dai; Xianhua Pan

doi:10.3390/molecules22040662

Improved Synthesis of 1-O-Acyl-β-d-Glucopyranose Tetraacetates

Molecules. 2017 Apr 21;22(4):662. doi: 10.3390/molecules22040662.

Authors

Yu Chen¹, Huan Lu², Yanyu Chen³, Wansheng Yu⁴, Hui Dai⁵, Xianhua Pan^{6

7}

Affiliations

¹ School of Perfume and Aroma Technology, Shanghai Institute of Technology, 100 Haiquan Rd., Shanghai 201418, China. chenyu@sit.edu.cn.
² Shanghai Research Institute of Fragrance and Flavor Industry, 480 Nanning Rd., Shanghai 200232, China. 156071203@mail.sit.edu.cn.
³ School of Perfume and Aroma Technology, Shanghai Institute of Technology, 100 Haiquan Rd., Shanghai 201418, China. aijiudu@sina.com.
⁴ Shanghai Research Institute of Fragrance and Flavor Industry, 480 Nanning Rd., Shanghai 200232, China. yu102658@126.com.
⁵ Shanghai Research Institute of Fragrance and Flavor Industry, 480 Nanning Rd., Shanghai 200232, China. ddai_hui@126.com.
⁶ School of Perfume and Aroma Technology, Shanghai Institute of Technology, 100 Haiquan Rd., Shanghai 201418, China. panxh@sit.edu.cn.
⁷ Shanghai Research Institute of Fragrance and Flavor Industry, 480 Nanning Rd., Shanghai 200232, China. panxh@sit.edu.cn.

Abstract

An improved synthesis of 1-O-acyl glucosyl esters that avoids the use of expensive Ag reagents as well as the hydrolysis of unstable glucosyl bromides is reported. Notably, β-configuration products were obtained exclusively in good yields.

Keywords: aliphatic acids; aromatic acids; glucosyl bromide; glucosyl esters.

MeSH terms

Acetates / chemical synthesis*
Acetates / chemistry
Esters / chemical synthesis*
Glucosides / chemical synthesis*
Glucosides / chemistry
Hydrolysis
Magnetic Resonance Spectroscopy
Structure-Activity Relationship

Substances

Acetates
Esters
Glucosides