A new look at acid catalyzed deacetylation of carbohydrates : A regioselective synthesis and reactivity of 2-O-acetyl aryl glycopyranosides

Show full item record



Permalink

http://hdl.handle.net/10138/311656

Citation

Stepanova , E V , Nagornaya , M O , Filimonov , V D , Valiev , R R , Belyanin , M L , Drozdova , A K & Cherepanov , V N 2018 , ' A new look at acid catalyzed deacetylation of carbohydrates : A regioselective synthesis and reactivity of 2-O-acetyl aryl glycopyranosides ' , Carbohydrate Research , vol. 458 , pp. 60-66 . https://doi.org/10.1016/j.carres.2018.02.003

Title: A new look at acid catalyzed deacetylation of carbohydrates : A regioselective synthesis and reactivity of 2-O-acetyl aryl glycopyranosides
Author: Stepanova, Elena V.; Nagornaya, Marina O.; Filimonov, Victor D.; Valiev, Rashid R.; Belyanin, Maxim L.; Drozdova, Anna K.; Cherepanov, Victor N.
Contributor: University of Helsinki, Department of Chemistry
Date: 2018-03-22
Language: eng
Number of pages: 7
Belongs to series: Carbohydrate Research
ISSN: 0008-6215
URI: http://hdl.handle.net/10138/311656
Abstract: Abstract In the present work we report that acetyl groups of per – acetylated aryl glycosides have different reactivity during the acidic deacetylation using HCl/EtOH in CHCl3, which leads to preferential deacetylation at O-3, O-4 and O-6. Thereby, the one-step preparation of 2-O-acetyl aryl glycosides with simple aglycon was accomplished for the first time. It was proved that the found reagent is to be general and unique for the preparation of series of 2-О-acetyl aryl glycosides. We have determined the influence of both carbohydrate moiety and the aglycon on the selectivity of deacetylation reaction by kinetic experiments. Using DFT/B3LYP/6-31G(d,p) and semi-empirical АМ1 methods we have found that the highest activation barrier is for 2-О-acetyl group. This completely explains the least reactivity of 2-О-acetyl group.
Subject: Aryl glycosides
Regioselective deacetylation
Reactivity
Partially acylated carbohydrates
Transition states modeling
MECHANISM
LEAVES
GROUP MIGRATION
CHEMOSELECTIVE DEACETYLATION
ACETYL GROUPS
CLEAVAGE
SALICIN
DERIVATIVES
BENZOYL
PHENOLIC GLYCOSIDES
116 Chemical sciences
Rights:


Files in this item

Total number of downloads: Loading...

Files Size Format View
1_s2.0_S0008621517309151_main.pdf 1.368Mb PDF View/Open

This item appears in the following Collection(s)

Show full item record