855662-13-4Relevant academic research and scientific papers
Synthesis of 12- O-Mono- and Diglycosyl-oxystearates, a New Class of Agonists for the C-type Lectin Receptor Mincle
Van Huy, Le,Tanaka, Chiaki,Imai, Takashi,Yamasaki, Sho,Miyamoto, Tomofumi
supporting information, p. 44 - 49 (2019/01/15)
Fifteen glycosyl-oxystearates were synthesized by Crich's 4,6-benzylidene and K?ening-Knorr strategies. Assessment of structure-activity relationships using macrophage-inducible C-type lectin (Mincle) receptor cells expressing nuclear factor of activated
Stannylene-mediated regioselective 6-O-glycosylation of unprotected phenyl 1-thioglycopyranosides
Maggi, Agnese,Madsen, Robert
, p. 2683 - 2691 (2013/06/05)
A straightforward procedure is described for the synthesis of (1→6)-linked saccharides by regioselective glycosylation of unprotected glycosyl acceptors. Phenyl 1-thioglycopyranosides derived from D-glucose, D-galactose and D-mannose were treated with dibutyltin oxide to introduce a stannylene acetal, and then subjected to selective glycosylation at the 6-position with the Koenigs-Knorr protocol. Peracylated glycosyl bromides of D-glucose, D-galactose, D-mannose and D-glucosamine were employed as the donors to give the corresponding (1→6)-linked disaccharides in moderate to good yields. The best results were obtained with glycosyl donors and acceptors derived from D-glucose and D-galactose. Fully acylated disaccharide thioglycosides could also serve as glycosyl donors for the regioselective coupling. Brominolysis and subsequent Koenigs-Knorr coupling with the stannylene acetal of phenyl 1-thio-β-D-glucopyranoside gave rise to the corresponding (1→6)-linked trisaccharides in moderate yields. Unprotected phenyl 1-thioglycopyranosides are activated with dibutyltin oxide and regioselectively glycosylated at the 6-position with peracylated glycosyl bromides under Koenigs-Knorr conditions. Copyright
