2-(Trimethylsilyl) ethyl glycosides. Transformation into glycopyranosyl chlorides

K Jansson, G Noori, G Magnusson

Index: Jansson, Karl; Noori, Ghazi; Magnusson, Goeran Journal of Organic Chemistry, 1990 , vol. 55, # 10 p. 3181 - 3185

Full Text: HTML

Citation Number: 83

Abstract

2-(Trimethylsily1) ethyl (TMSET) glycosides were transformed in high yields into the corresponding 1-chloro sugars by treatment with 1, l-dichloromethyl methyl ether/zinc chloride. With acetyl, benzoyl, and benzyl protection of the 2-position, the a-glycopyranosyl chloride was the major product, whereas with the 2-phthalimido sugar 13, the@-chloride 21 was obtained. The fully benzylated TMSET glucopyranoside 1 gave the a-chloro sugar 22 ...

Related Articles:

Differently N-protected 3, 4, 6-tri-O-acetyl-2-amino-2-deoxy-D-glucopyranosyl chlorides and their application in the synthesis of diosgenyl 2-amino-2-deoxy-β-D- …

[Bednarczyk, Dorota; Walczewska, Agata; Grzywacz, Daria; Sikorski, Artur; Liberek, Beata; Myszka, Henryk Carbohydrate Research, 2013 , vol. 367, p. 10 - 17]

Conversion of p-methoxyphenyl glycosides into the corresponding glycosyl chlorides and bromides, and into thiophenyl glycosides

[Zhang, Zhiyuan; Magnusson, Goeran Carbohydrate Research, 1996 , vol. 295, p. 41 - 55]

A facile and stereoselective synthesis of 3, 4, 6-tri-O-acetyl-2-deoxy-2phthalimido-β-D-glucopyranosyl chloride

[Journal of Chemical Research, , vol. 37, # 8 p. 467 - 469]

A convenient synthetic route to the disaccharide repeating-unit of peptidoglycan

[Carbohydrate research, , vol. 162, # 2 p. 227 - 235]

Differently N-protected 3, 4, 6-tri-O-acetyl-2-amino-2-deoxy-D-glucopyranosyl chlorides and their application in the synthesis of diosgenyl 2-amino-2-deoxy-β-D- …

[Bednarczyk, Dorota; Walczewska, Agata; Grzywacz, Daria; Sikorski, Artur; Liberek, Beata; Myszka, Henryk Carbohydrate Research, 2013 ,  vol. 367, p. 10 - 17]

More Articles...