Stereoselective Syntheses of. ALPHA.-Glucuronides Using Dehydrative Glycosylation.

…, A Tomaru, M Iida, M Kanemitsu, K Takenaka…

Index: Koto, Shinkiti; Miura, Teruhisa; Hirooka, Motoko; Tomaru, Aya; Iida, Mika; Kanemitsu, Masanori; Takenaka, Kazuhiro; Masuzawa, Shinichi; Miyaji, Saeko; Kuroyanagi, Naoko; Yagishita, Miki; Zen, Shonosuke; Yago, Kazuo; Tomonaga, Fumiya Bulletin of the Chemical Society of Japan, 1996 , vol. 69, # 11 p. 3247 - 3259

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Citation Number: 13

Abstract

Methyl and benzyl 2, 3, 4-tri-O-benzyl-D-glucopyranuronates, prepared from D-glucurono-6, 3-lactone, afforded selectively the corresponding α-glucopyranosiduronates by the aid of the condensing reagent system composed of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine. Using this method, O-α-D-glucopyranuronosyl- (1→ 3)-O-α-L-arabinofuranosyl-(1→ 3)-D-xylopyranose, one of the minimal component ...