Abstract
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.
| Original language | English |
|---|---|
| Article number | 6972 |
| Pages (from-to) | 36-40 |
| Number of pages | 5 |
| Journal | Carbohydrate Research |
| Volume | 409 |
| DOIs | |
| Publication status | Published - 29 May 2015 |
Keywords
- Aryl 2′-O-acetyl d-glucopyranoside
- Phenolic acyl glycosides
- Salireposide
ASJC Scopus subject areas
- Analytical Chemistry
- Biochemistry
- Organic Chemistry
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Stepanova, E. V., Belyanin, M. L., Filimonov, V. D., Valiev, R. R., Gruner, M., & Rogachev, V. (2015). The first example of a one-step synthesis of 2′-O-acetyl aryl-D-glucopyranosides. Carbohydrate Research, 409, 36-40. [6972]. https://doi.org/10.1016/j.carres.2015.03.017