Journal ArticleDOI
Studies on unsaturated sugars with particular reference to the synthesis of 6-Deoxy-6-fluoro derivatives
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Three fluoro-substituted unsaturated sugars have been synthesized by transformations within the D-glucal and ethyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside series.Abstract:
Three fluoro-substituted unsaturated sugars have been synthesized by transformations within the D-glucal and ethyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside series. A number of the intermediate unsaturated sugars not previously described have been characterized. The advantages of the t-butyldimethylsilyl blocking group in such syntheses are described.read more
Citations
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Journal ArticleDOI
Displacement reactions of a 1,2-anhydro-α-d-hexopyranose: installation of useful functionality at the anomeric carbon
Book ChapterDOI
Synthesis and reactions of unsaturated sugars.
Robert J. Ferrier,John O. Hoberg +1 more
TL;DR: This chapter surveys the chemistry of most of the important types of monosaccharide derivatives that contain single alkene groups—notably, the glycols that are extremely valuable starting materials for a vast range of synthetic transformations.
Journal ArticleDOI
Glycosylimidate, 16. Synthese des Trisaccharids aus der „Repeating Unit”︁ des Kapselpolysaccharids von Neisseria meningitidis (Serogruppe L)
Willy Kinzy,Richard R. Schmidt +1 more
TL;DR: In this article, the trisaccharide β-D-GlcNAc was transformed into the per-O-acetylated trisACcharide α-trichloroacetimidate by removing the 1-Osilyl protective group, reduction of the azido groups, hydrogenolytic debenzylation, and peracetylation.
Journal ArticleDOI
Preparation of pyranoid glycal derivatives from phenyl thioglycosides and glycosyl phenyl sulphones
TL;DR: In this article, a pyranoid glycal derivatives with acid-labile protecting groups (acetal, ether, ester) were obtained in excellent yields, and a β-linked 2′-deoxydisaccharide glycal derivative was also prepared from the corresponding disaccharides phenyl thioglycoside.
Journal ArticleDOI
Total synthesis of the potential anticancer vaccine KH-1 adenocarcinoma antigen
TL;DR: The successful total synthesis of an adenocarcinoma antigen, KH-1, and of a bioconjugatable analogue which can bind to a carrier protein are presented and illustrate the capabilities of oligosaccharide synthesis for reconstructing the challenging structural motifs characteristic of carbohydrate antigens.