496924-01-7Relevant academic research and scientific papers
Syntheses of N-aryl-protected glucosamines and their stereoselectivity in chemical glycosylations
Otsuka, Yuji,Yamamoto, Toshihiro,Fukase, Koichi
, p. 3019 - 3023 (2017/07/17)
N-Aryl-protecting groups were introduced in glucosamines to achieve β-selective glycosylation. Various N-aryl aminosugars were synthesized via Buchwald–Hartwig reaction. Glycosylation using glycosyl trichloroacetimidates of N-aryl aminosugars smoothly proceeded in the presence of trimethylsilyl trifluoromethanesulfonate. Use of a glycosyl donor comprising an electron-donating 2,4-dimethoxyphenyl (DMP) group led to the glycosylation proceeding with high β selectivity. This stereoselectivity seemed to be derived from the formation of an aziridine intermediate. The DMP-protecting group can be removed immediately by using ammonium hexanitratocerate (IV).
Influence on the enantioselectivity in allylic alkylation of the anomeric position of the phosphine-amide ligands derived from d-glucosamine
Glego?a, Katarzyna,Framery, Eric,Goux-Henry, Catherine,Micha? Pietrusiewicz,Sinou, Denis
, p. 7133 - 7141 (2008/02/07)
The synthesis of a new series of chiral phosphine amides derived from d-glucosamine is described. The palladium-catalyzed asymmetric allylic alkylations of racemic (E)-1,3-diphenyl-2-propenyl acetate with dimethyl malonate using these ligands have been in
