TY - JOUR
T1 - The first example of a one-step synthesis of 2′-O-acetyl aryl-D-glucopyranosides
AU - Stepanova, Elena Vledimirovna
AU - Belyanin, Maxim L.
AU - Filimonov, Victor D.
AU - Valiev, Rashid R.
AU - Gruner, Margit
AU - Rogachev, Victor
PY - 2015/5/29
Y1 - 2015/5/29
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.
KW - Aryl 2′-O-acetyl d-glucopyranoside
KW - Phenolic acyl glycosides
KW - Salireposide
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U2 - 10.1016/j.carres.2015.03.017
DO - 10.1016/j.carres.2015.03.017
M3 - Article
AN - SCOPUS:84929470557
VL - 409
SP - 36
EP - 40
JO - Carbohydrate Research
JF - Carbohydrate Research
SN - 0008-6215
M1 - 6972
ER -