The first example of a one-step synthesis of 2'-O-acetyl aryl-D-glucopyranosides

Elena V Stepanova; Maxim L Belyanin; Victor D Filimonov; Rashid R Valiev; Margit Gruner; Victor Rogachev

doi:10.1016/j.carres.2015.03.017

The first example of a one-step synthesis of 2'-O-acetyl aryl-D-glucopyranosides

Carbohydr Res. 2015 May 29:409:36-40. doi: 10.1016/j.carres.2015.03.017. Epub 2015 Apr 8.

Authors

Elena V Stepanova¹, Maxim L Belyanin², Victor D Filimonov², Rashid R Valiev³, Margit Gruner⁴, Victor Rogachev⁵

Affiliations

¹ Department of Biotechnology and Organic Chemistry, National Research Tomsk Polytechnic University, 30 Lenin Avenue, Tomsk 634050, Russia. Electronic address: eline_m@mail.ru.
² Department of Biotechnology and Organic Chemistry, National Research Tomsk Polytechnic University, 30 Lenin Avenue, Tomsk 634050, Russia.
³ Department of General and Inorganic Chemistry, National Research Tomsk Polytechnic University, 30 Lenin Avenue, Tomsk 634050, Russia; Tomsk State University, Lenina Avenue 36, Tomsk 634050, Russia.
⁴ Professur für Organische Chemie I, Technische Universität Dresden, 01062 Dresden, Germany.
⁵ Department of Biotechnology and Organic Chemistry, National Research Tomsk Polytechnic University, 30 Lenin Avenue, Tomsk 634050, Russia; Professur für Organische Chemie I, Technische Universität Dresden, 01062 Dresden, Germany.

PMID: 25950119
DOI: 10.1016/j.carres.2015.03.017

Abstract

A selective acidic system for partial deacetylation of phenolic d-glucopyranosides per-acetates has been developed that allows synthesis of the corresponding 2'-O-acetyl-D-glucosides. Many disadvantages of generally used methods for preparing such mono-acyl derivatives involving multistep procedures or the use of enzymes are avoided. The ion at m/z 289 in mass spectra of their TMS derivatives indicates a particular and characteristic fragmentation pattern of these 2'-O-acetyl derivatives of d-glucopyranosides. Quantum-chemical calculations applying B3LYP/TZVP level of theory revealed the stability of 2'-O-acetyl glucopyranoside if compare with 3'-, 4'- and 6'- O-acetyl glucopyanosides.

Keywords: Aryl 2′-O-acetyl d-glucopyranoside; Phenolic acyl glycosides; Salireposide.

Publication types

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

MeSH terms

Glucosides / chemical synthesis*
Glucosides / chemistry
Glycosides / chemical synthesis*
Glycosides / chemistry

Substances

Glucosides
Glycosides