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 |
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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 journal › Article
}
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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UR - http://www.scopus.com/inward/citedby.url?scp=84929470557&partnerID=8YFLogxK
U2 - 10.1016/j.carres.2015.03.017
DO - 10.1016/j.carres.2015.03.017
M3 - Article
VL - 409
SP - 36
EP - 40
JO - Carbohydrate Research
JF - Carbohydrate Research
SN - 0008-6215
M1 - 6972
ER -