84635-46-1Relevant 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).
Stereoselective Synthesis of Mixed Acetal Glycosides by Reaction of Tri-O-acetyl-N-(2,4-dinitrophenyl)-α-D-glucosaminyl Bromide with Alcohol in Acetone
Koto, Shinkiti,Inada, Shigeru,Narita, Tomoko,Morishima, Naohiko,Zen, Shonosuke
, p. 3665 - 3666 (2007/10/02)
Some mixed acetal glycosides were stereoselectively synthesized by the reaction of 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitroanilino)-α-D-glucopyranosyl bromide with alcohols in acetone containing Hg(CN)2, HgBr2, and tetrabutylammonium bromide at room temperature.When t-butyl alcohol was used, a novel enol glycoside of acetone was formed.
