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

Research output: Contribution to journalArticle

4 Citations (Scopus)

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 languageEnglish
Article number6972
Pages (from-to)36-40
Number of pages5
JournalCarbohydrate Research
Volume409
DOIs
Publication statusPublished - 29 May 2015

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Derivatives
Glucosides
Acetates
Ions
Enzymes

Keywords

  • Aryl 2′-O-acetyl d-glucopyranoside
  • Phenolic acyl glycosides
  • Salireposide

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

Cite this

The first example of a one-step synthesis of 2′-O-acetyl aryl-D-glucopyranosides. / Stepanova, Elena Vledimirovna; Belyanin, Maxim L.; Filimonov, Victor D.; Valiev, Rashid R.; Gruner, Margit; Rogachev, Victor.

In: Carbohydrate Research, Vol. 409, 6972, 29.05.2015, p. 36-40.

Research output: Contribution to journalArticle

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AU - Stepanova, Elena Vledimirovna

AU - Belyanin, Maxim L.

AU - Filimonov, Victor D.

AU - Valiev, Rashid R.

AU - Gruner, Margit

AU - Rogachev, Victor

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N2 - 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.

AB - 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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