33585-16-9Relevant articles and documents
Macrocyclic derivatives with a sucrose scaffold: insertion of a long polyhydroxylated linker between the terminal 6,6′-positions
Chaciak, Bartosz,D?browa, Kajetan,Swider, Pawe?,Jarosz, S?awomir
, p. 18578 - 18584 (2018)
A series of five new macrocyclic hybrids with a sucrose scaffold were prepared by the reaction of activated 1′,2,3,3′,4,4′-hexa-O-methylsucrose with diversely functionalized d-mannitols. The 21-, 25-, and 31-membered representatives containing mannitol units were prepared by a macrocyclization of 6,6′-di-O-propargylated sucrose with protected 1,6-diazido-d-mannitol or 6,6′-di-azidosucrose with propargylated d-mannitol (a “click” approach), whereas 23-membered representatives were prepared by double N-alkylation of 1′,2,3,3′,4,4′-hexa-O-methyl-6,6′-di-aminosucrose with 1,6-di-bromoacyl d-mannitol. All sucrose derivatives were tested as putative hosts for chiral recognition of α-phenylethylammonium (α-PEA) cations. In one case, in striking contrast to all sucrose-based macrocyclic hosts previously reported by us, unexpected reverse preference for the R-enantiomer was observed (KR/KS = 1.5).
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.
CuAAC-mediated diversification of aminoglycoside-arginine conjugate mimics by non-reducing di- and trisaccharides
Westermann, Bernhard,D?rner, Simon,Brauch, Sebastian,Schaks, Angela,Heinke, Ramona,Stark, Sebastian,Van Delft, Floris L.,Van Berkel, Sander S.
, p. 61 - 67 (2013/05/09)
Di- and triguanidinylation of trehalose, sucrose, and melizitose has been achieved via a Huisgen-cycloaddition approach. They can serve as aminoglycoside-arginine conjugate mimics, which has been demonstrated by their biological profiles in assays against
