PMID: 2507141Jul 1, 1989Paper

Synthesis of galactofuranose disaccharides of biological significance

Carbohydrate Research
C MarinoR M de Lederkremer

Abstract

Methyl beta-D-galactofuranoside was readily obtained by tin(IV) chloride-catalyzed glycosylation of penta-O-benzoyl-alpha,beta-D-galactofuranose, followed by debenzoylation with sodium methoxide. Glycosylation of 1 with 2,3,5-tri-O-benzoyl-D-galactono-1,4-lactone or with the 6-O-trityl-lactone derivative 5 gave the benzoylated beta-D-galactofuranosyl-(1----6)-D-galactono-1,4-lactone 6 in excellent yield. The structure of disaccharide 6 was confirmed by borohydride reduction to the glycosyl-alditol 7. A byproduct of the condensation reaction of 1 with 4 or 5 was identified as the benzoylated (1----1)-beta,beta'-D-galactofuranosyl disaccharide 8. Compound 8 was readily prepared (88% yield) by controlled addition of water to 1, in the presence of stannic chloride. O-Debenzoylation of 8 afforded crystalline beta'-D-galactofuranosyl-(1----1)-beta-D-galactofuranoside. The glycosyl-lactone 6 constitutes a key intermediate for the synthesis of a disaccharide derivative having both units in the furanoid form. Thus, diisoamylborane reduction of the lactone function of 6 led to the disaccharide derivative 10, from which the methyl glycoside 12 was prepared. O-Debenzoylation of 12 gave the corresponding methyl beta-D-galactofuranosyl-(1---...Continue Reading

Citations

Jun 13, 2013·Chemico-biological Interactions·Guilherme L SassakiPhilip A J Gorin
Jun 14, 2016·Accounts of Chemical Research·Todd L Lowary
Jan 15, 2014·Chembiochem : a European Journal of Chemical Biology·Carla Marino, Luciana Baldoni
Sep 9, 2017·Future Science OA·Carla MarinoRosa M de Lederkremer
May 21, 2008·The Journal of Organic Chemistry·Gladys C Completo, Todd L Lowary
Jun 14, 1996·The Journal of Organic Chemistry·Christián Di NardoOscar Varela
Apr 25, 1990·Carbohydrate Research·R M de LederkremerO Varela
Oct 25, 2003·The Journal of Organic Chemistry·Morwenna S M PearsonDavid Deniaud
Mar 8, 1996·The Journal of Organic Chemistry·Carola Gallo-RodriguezRosa M. de Lederkremer
Jan 2, 2010·Carbohydrate Research·Verónica M MendozaCarola Gallo-Rodriguez
Jun 15, 2010·Bioorganic & Medicinal Chemistry·Andrea BordoniCarla Marino

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