Tetrahedron Letters

Einfache und stereoselektive synthese von α-und β-phenylglykosiden

LF Tietze, HJ Guder

Index: Tietze, Lutz-F.; Fischer, Roland; Guder, Hans-Joachim Tetrahedron Letters, 1982 , vol. 23, # 45 p. 4661 - 4664

Full Text: HTML

Citation Number: 50

Abstract

Abstract Reaction of phenyl-trimethylsilylethers (3) with 1-O-trimethylsilyl-2, 3, 4, 6-tetra-O- acetyl-D-glucoside (1)(anomeric mixture) yields almost exclusively the aryl-β-glucosides (4) in the presence of catalytic amounts of TMS-triflate at 20 C, whereas (3) and 1-O- trimethylsilyl-2, 3, 4, 6-tetra-O-benzyl-D-glucoside (2) gives mainly the aryl-α-glucosides (8).

Related Articles:

Revisit of the phenol O-glycosylation with glycosyl imidates, BF 3· OEt 2 is a better catalyst than TMSOTf

[Li, Yali; Mo, Huaping; Lian, Gaoyan; Yu, Biao Carbohydrate Research, 2012 , vol. 363, p. 14 - 22]

Stereoselectivity of Reactions at the Glycoside Center of Carbohydrates: VII. Synthesis of Aryl α-and-β-D-Glucopyranosides by Helferich, Catalyzed by Boron …

[Sokolov; Zakharov; Studentsov Russian Journal of General Chemistry, 2002 , vol. 72, # 5 p. 806 - 811]

3-Demethoxy-3-glycosylaminothiocolchicines: synthesis of a new class of putative muscle relaxant compounds

[Yamaguchi, Masahiko; Horiguchi, Akira; Fukuda, Akira; Minami, Toru Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990 , # 4 p. 1079 - 1082]

More Articles...