6907-84-2Relevant academic research and scientific papers
THERMAL GLYCOSIDATION WITH BENZYLATED GLYCOSYL CHLORIDES: A VERY SIMPLE PROCEDURE FOR O-GLYCOSIDATION
Nishizawa, Mugio,Kan, Yukiko,Yamada, Hidetoshi
, p. 565 - 567 (2007/10/02)
Thermal condensation of benzylated glucosyl chlorides with a variety of alcohols has been achieved efficiently without using any metal salts via a simple operation, and the procedure is used not only for a glucosyl halide, but also for a xylosyl chloride. KEYWORDS O-glycosidation; thermal glycosidation; glucosyl chloride; xylosyl chloride; disaccharide
Glycoside Synthesis Using 2,3,4,6-Tetra-O-pivaloyl-α-D-glucopyranosyl Bromide
Kunz, Horst,Harreus, Albrecht
, p. 41 - 48 (2007/10/02)
In the presence of silver salts the glycosylation of benzyl alcohol and of cholesterol is achieved in high yields by use of 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide (2).The formation of orthoesters, which often complicates the Koenigs-Knorr reaction using 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (5), is largely suppressed using 2.The preferential formation of the glycoside from the intermediate ion A is a result of the steric influence of the tert-butyl substituent which hinders nucleophilic attack at the acyloxonium carbon atom and steers the reaction in the desired direction.
SYNTHESIS OF TRITERPENE AND STEROID GLYCOSIDES
Uvarova, Nina I.,Atopkina, Lyubov N.,Elyakov, Georgi B.
, p. 33 - 42 (2007/10/02)
The glycosylation of cholesterol, β-sitosterol, 28-O-acetylbetulin, and betulin with acylated glycosyl halides in the presence of Hg(OAc)2, Hg(CN)2, CdCO3, Ag2O, Ag2CO3, and HgO + HgBr2 usually gives acylated αβ-glycosides accompanied by acetates, ethers, and bromo and unsaturated derivatives of the initial alcohols.The use of Hg(CN)2 gave mainly β anomers (40-87percent), whereas α anomers preponderated when Hg(OAc)2 was the catalyst.When there was a deficiency of hydrogen halide acceptor and in the presence of the acidic catalyst HgBr2*HBr, the β anomer, produced initially, underwent anomerisation.Cholesteryl α-D-glucopyranoside tetra-acetate (48percent) was obtained by anomerisation of the β anomer.
