Synthesis of the trisaccharide portion of soyasaponin beta g: evaluation of a new glucuronic acid acceptor |
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Authors: | Plé Karen |
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Affiliation: | Laboratoire de Pharmacognosie, Université de Reims Champagne-Ardenne, CNRS UMR 6013, CPCBAI, Bat. 18, Moulin de la Housse, BP 1039, F-51687 Reims, France. karen.ple@univ-reims.fr |
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Abstract: | The synthesis of the trisaccharide portion of soyasaponin beta g was successfully achieved using a new glucuronic acid acceptor: methyl 1-O-allyl-3,4-di-O-methoxymethyl-beta-D-glucuronate (9). This compound and methyl 1-O-allyl-3,4-di-O-tert-butyldimethylsilyl-beta-D-glucuronate (8) were both prepared from glucuronolactone via a glycal intermediate. The former compound 9 was successfully coupled to ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-beta-D-galactopyranoside (13) in excellent yield. Synthesis of the protected trisaccharide was then completed by the addition of a suitably protected rhamnose derivative to the disaccharide portion. The reactivity of the glucuronic acid derivative 9 was also explored with trichloroacetimidate and fluoride donors. |
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Keywords: | DDMP saponins Glucuronic acid glycosylation Saponin synthesis |
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