81086-93-3Relevant academic research and scientific papers
Aqueous Glycosylation of Unprotected Sucrose Employing Glycosyl Fluorides in the Presence of Calcium Ion and Trimethylamine
Pelletier, Guillaume,Zwicker, Aaron,Allen, C. Liana,Schepartz, Alanna,Miller, Scott J.
, p. 3175 - 3182 (2016/03/19)
We report a synthetic glycosylation reaction between sucrosyl acceptors and glycosyl fluoride donors to yield the derived trisaccharides. This reaction proceeds at room temperature in an aqueous solvent mixture. Calcium salts and a tertiary amine base promote the reaction with high site-selectivity for either the 3′-position or 1′-position of the fructofuranoside unit. Because nonenzymatic aqueous oligosaccharide syntheses are underdeveloped, mechanistic studies were carried out in order to identify the origin of the selectivity, which we hypothesized was related to the structure of the hydroxyl group array in sucrose. The solution conformation of various monodeoxysucrose analogs revealed the co-operative nature of the hydroxyl groups in mediating both this aqueous glycosyl bond-forming reaction and the site-selectivity at the same time.
Library of mild and economic protocols for the selective derivatization of sucrose under microwave irradiation
Barros, M. Teresa,Petrova, Krasimira T.,Correia-Da-Silva, Paula,Potewar, Taterao M.
, p. 1897 - 1906 (2011/09/19)
The chemistry of sucrose is very challenging due to its eight hydroxyl groups, three of which are primary, with very similar reactivities, thus control of the chemoselectivity is a central issue. In this work, the selective formation of monounsaturated es
Facile conversion of O-silyl protected sugars into their corresponding formates using POCl3·DMF complex
Andrade, Marta M.,Barros, M. Teresa
, p. 9235 - 9243 (2007/10/03)
The direct O-formylation of two selectively protected sugar derivatives using the Vilsmeier-Haack (V-H) complex POCl3·DMF was studied. Primary O-TBDMS and O-TBDPS ethers of sucrose, the most common disaccharide, underwent regio and chemoselecti
