The first example of a one-step synthesis of 2'-O-acetyl aryl-D-glucopyranosides
Elena V Stepanova1, Maxim L Belyanin1, Victor D Filimonov1
1Department of Biotechnology and Organic Chemistry, National Research Tomsk Polytechnic University, 30 Lenin Avenue, Tomsk 634050, Russia.
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.
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