Publication

Synthesis of a C-disaccharide analog of the Thomsen-Friedenreich (T) epitope

Pierre Vogel
2001
Journal Articles

Abstract

The 2,3,4,6-tetra-O-[(tert-butyl)dimethylsilyl]-C-beta -D- galactopyranosylformaldehyde (2,6-anhydro-1,3,4,6-tetra-O-[(tert-butyl)dimethylsilyl]-D-glycero-L-man no-heptose, 2) was condensed with isolevoglucosenone (3) in the presene e of Et(2)AII to give 1,6-anhydro-3-C- {(1R)-2,6-anhydro-3,4,5,7-tetra-O-[(tert-butyl)dimethylsilyl]-D-glycero- L-manno-heptitol-1-C-yl}-2,3-dideoxy-beta -D-glycero-hex-2-enopyranos-4-ulose (8). Diastereoselective conjugate addition of BnONHBn to 8, followed by diastereoselective ketone reduction with LiBH4 and treatment with Me3SiSPh/ZnI2, provided phenyl 3-C-{(1R)-2,6-anhydro-3,4,5,7-tetra-O[(tert-butyl)dimethylsilyl]-D-glyce ro-L-manno-heptitol-1-C-yl}-2-[ (N-benzoxyl-N-benzyl)amino]-2,3-dideoxy-1-thio-beta -D-galacto-hexopyranoside (14).

Official source

https://infoscience.epfl.ch/entities/publication/c0eb38f7-0de0-4e91-a3f6-2640b46679e7

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Pierre Vogel
2001
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/c0eb38f7-0de0-4e91-a3f6-2640b46679e7

About this result

Related concepts (6)

Monosaccharide

Monosaccharides (from Greek monos: single, sacchar: sugar), also called simple sugars, are the simplest forms of sugar and the most basic units (monomers) from which all carbohydrates are built. They are usually colorless, water-soluble, and crystalline solids. Contrary to their name (sugars), only some monosaccharides have a sweet taste. Most monosaccharides have the formula (CH2O) (though not all molecules with this formula are monosaccharides). Examples of monosaccharides include glucose (dextrose), fructose (levulose), and galactose.

Glucose

Glucose is a sugar with the molecular formula . Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using energy from sunlight, where it is used to make cellulose in cell walls, the most abundant carbohydrate in the world. In energy metabolism, glucose is the most important source of energy in all organisms. Glucose for metabolism is stored as a polymer, in plants mainly as starch and amylopectin, and in animals as glycogen.

Glycosidic bond

A glycosidic bond or glycosidic linkage is a type of ether bond that joins a carbohydrate (sugar) molecule to another group, which may or may not be another carbohydrate. A glycosidic bond is formed between the hemiacetal or hemiketal group of a saccharide (or a molecule derived from a saccharide) and the hydroxyl group of some compound such as an alcohol. A substance containing a glycosidic bond is a glycoside.