153062-19-2Relevant 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
, 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
Synthesis of a mannotetraose derivative related to the antigen from Escherichia coli O9a:K26:H-
Misra, Anup Kumar,Roy, Nirmolendu
, p. 308 - 311 (2007/10/03)
The disaccharide blocks ethyl O-(2, 3, 4, 6-tetra-O-acetyl-α-D-mannopyranosyl)-(1 → 3)-2-O-acetyl-4, 6-O-benzylidene-1-thio-α-D-mannopyranoside 7 and methyl O-(3-O-benzyl-4, 6-O-benzylidene-α-D-mannopyranosyl)-(1 → 2)-3-Obenzyl-4, 6-O-benzylidene-α-D-mann
Chemistry of 1-alkoxy-1-glycosyl radicals: The manno- and rhamnopyranosyl series. Inversion of α- to β-pyranosides and the fragmentation of anomeric radicals
Crich, David,Sun, Sanxing,Brunckova, Jarmila
, p. 605 - 615 (2007/10/03)
The formation and stereoselective quenching of 1-mannopyranosyl radicals by a tributyltin hydride-mediated intramolecular 1,5-hydrogen abstraction sequence is described. A competing process is 1,4-hydrogen atom abstraction leading principally to glucopyran-2-ulosides. Fragmentation of the anomeric radical resulting in the formation of ring opened products is a problem in certain series. The chemistry is dictated to a considerable extent by the nature of the protecting groups employed with the 4,6-benzylidene series and, for rhamnose, the Ley 3,4-dispiroketal, being particularly susceptible to the 1,4-hydrogen atom abstraction but less to the fragmentation. Photochemical conditions are described, in which these side reactions are practically eliminated, and applied to the inversion of an α- to a β-mannoside in a disaccharide.
