Abstract
The total synthesis of certain natural phenolglycosides of the family Salicaceae, namely: salireposide, populosides A, B, and C and not occurring in plants desoxysalireposide (2-(β-d-glucopyranosyloxy)-benzylbenzoate) and per-acetate of iso-salireposide (2-(β-d-glucopyranosyloxy)-5-benzoyloxy benzyl alcohol), starting from readily available phenols and glucose was accomplished. A simple method for the synthesis of phenolglycosides derivatives of 2-acyloxy salicyl and gentisyl alcohol was developed. The key step of these natural products' synthesis is a selective removal of acetyl groups in the presence of other acyl groups.
| Original language | English |
|---|---|
| Pages (from-to) | 66-72 |
| Number of pages | 7 |
| Journal | Carbohydrate Research |
| Volume | 363 |
| DOIs | |
| Publication status | Published - 1 Dec 2012 |
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Keywords
- Glycosylation
- Phenolic glycosides
- Populosides A, B, C
- Protective group cleavage
- Salireposide
ASJC Scopus subject areas
- Analytical Chemistry
- Biochemistry
- Organic Chemistry
Cite this
First total chemical synthesis of natural acyl derivatives of some phenolglycosides of the family Salicaceae. / Belyanin, Maxim L.; Stepanova, Elena Vledimirovna; Ogorodnikov, Vladimir D.
In: Carbohydrate Research, Vol. 363, 01.12.2012, p. 66-72.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - First total chemical synthesis of natural acyl derivatives of some phenolglycosides of the family Salicaceae
AU - Belyanin, Maxim L.
AU - Stepanova, Elena Vledimirovna
AU - Ogorodnikov, Vladimir D.
PY - 2012/12/1
Y1 - 2012/12/1
N2 - The total synthesis of certain natural phenolglycosides of the family Salicaceae, namely: salireposide, populosides A, B, and C and not occurring in plants desoxysalireposide (2-(β-d-glucopyranosyloxy)-benzylbenzoate) and per-acetate of iso-salireposide (2-(β-d-glucopyranosyloxy)-5-benzoyloxy benzyl alcohol), starting from readily available phenols and glucose was accomplished. A simple method for the synthesis of phenolglycosides derivatives of 2-acyloxy salicyl and gentisyl alcohol was developed. The key step of these natural products' synthesis is a selective removal of acetyl groups in the presence of other acyl groups.
AB - The total synthesis of certain natural phenolglycosides of the family Salicaceae, namely: salireposide, populosides A, B, and C and not occurring in plants desoxysalireposide (2-(β-d-glucopyranosyloxy)-benzylbenzoate) and per-acetate of iso-salireposide (2-(β-d-glucopyranosyloxy)-5-benzoyloxy benzyl alcohol), starting from readily available phenols and glucose was accomplished. A simple method for the synthesis of phenolglycosides derivatives of 2-acyloxy salicyl and gentisyl alcohol was developed. The key step of these natural products' synthesis is a selective removal of acetyl groups in the presence of other acyl groups.
KW - Glycosylation
KW - Phenolic glycosides
KW - Populosides A, B, C
KW - Protective group cleavage
KW - Salireposide
UR - http://www.scopus.com/inward/record.url?scp=84868261321&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84868261321&partnerID=8YFLogxK
U2 - 10.1016/j.carres.2012.10.006
DO - 10.1016/j.carres.2012.10.006
M3 - Article
C2 - 23123575
AN - SCOPUS:84868261321
VL - 363
SP - 66
EP - 72
JO - Carbohydrate Research
JF - Carbohydrate Research
SN - 0008-6215
ER -