title: The first example of a one-step synthesis of 2'-O-acetyl aryl-D-glucopyranosides.
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.
authors.affiliation: Department of Biotechnology and Organic Chemistry, National Research Tomsk Polytechnic University, 30 Lenin Avenue, Tomsk 634050, Russia. Electronic address: eline_m@mail.ru.
authors.forename: Elena V
authors.initials: EV
authors.lastname: Stepanova
authors.affiliation: Department of Biotechnology and Organic Chemistry, National Research Tomsk Polytechnic University, 30 Lenin Avenue, Tomsk 634050, Russia.
authors.forename: Maxim L
authors.initials: ML
authors.lastname: Belyanin
authors.affiliation: Department of Biotechnology and Organic Chemistry, National Research Tomsk Polytechnic University, 30 Lenin Avenue, Tomsk 634050, Russia.
authors.forename: Victor D
authors.initials: VD
authors.lastname: Filimonov
authors.affiliation: 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.
authors.forename: Rashid R
authors.initials: RR
authors.lastname: Valiev
authors.affiliation: Professur für Organische Chemie I, Technische Universität Dresden, 01062 Dresden, Germany.
authors.forename: Margit
authors.initials: M
authors.lastname: Gruner
authors.affiliation: 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.
authors.forename: Victor
authors.initials: V
authors.lastname: Rogachev
mesh_terms: D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D005960:Glucosides; D006027:Glycosides
keywords: Aryl 2′-O-acetyl d-glucopyranoside; Phenolic acyl glycosides; Salireposide