The first example of a one-step synthesis of 2′-O-acetyl aryl-d-glucopyranosides

• Selective acidic deacetylation of fully acetylated phenolic glycosides esters gives only the 2′-acetate.
• Tri-O-TMS-derivatives of the 2′-O-acetyl aryl glycosides show a specific ion at m/z 289 in their mass spectra.
• Previously unavailable monoacetyl-derivatives of phenyl glucopyranosides were obtained.
• Quantum-≿hemical calculations confirmed the stability of 2′-O-acetyl glucopyranosides.

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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