STEREOSELECTIVE SYNTHESES OF ALPHA-GLUCURONIDES USING DEHYDRATIVE GLYCOSYLATION

Authors
KOTO S MIURA T HIROOKA M TOMARU A IIDA M KANEMITSU M TAKENAKA K MASUZAWA S MIYAJI S KUROYANAGI N YAGISHITA M ZEN S YAGO K TOMONAGA F
Citation
S. Koto et al., STEREOSELECTIVE SYNTHESES OF ALPHA-GLUCURONIDES USING DEHYDRATIVE GLYCOSYLATION, Bulletin of the Chemical Society of Japan, 69(11), 1996, pp. 3247-3259
Citations number
71
Categorie Soggetti
Chemistry
Journal title
Bulletin of the Chemical Society of Japan → ACNP
ISSN journal
00092673
Volume
69
Issue
11
Year of publication
1996
Pages
3247 - 3259
Database
ISI
SICI code
0009-2673(1996)69:11<3247:SSOAUD>2.0.ZU;2-J
Abstract
Methyl and benzyl 2,3,4-tri-O-benzyl-D-glucopyranuronates, prepared fr om D-glucurono-6,3-lactone, afforded selectively the corresponding alp ha-glucopyranosiduronates by the aid of the condensing reagent system composed of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesu lfonate, and triethylamine. Using this method, copyranuronosyl-(1-->3) -O-alpha-L-arabinofuranosyl one of the minimal component units in the structure of plantago-mucilage A from the seeds of Plantago asiatica L inne constituting a Chinese medicine:chegianzi (sic).