Publication

Synthesis of (1 -> 3)-C and homo(1 -> 3)-C-linked iminodisaccharides starting from levoglucosenone and isolevoglucosenone

Pierre Vogel
2002
Journal Articles

Abstract

The reaction of 2,5-(benzyloxycarbonyl)imino-2,5-dideoxy-3,4-O-isopropylidene-L-ribose ((-)-15) with levoglucosenone (5) in the presence of Et2AlI gave a 3,4-dideoxy-D-glycero-hex-3-enopyranos-2-ulose derivative ((-)-16) that was converted into the (1-->3)-C-linked imino-disaccharide: methyl 3,4-dideoxy-3-[(1'S)-2',5'-dideoxy-2',5'-imino-D-ribitol-1'-C-yl)-alpha- D-lyxo-hexo-pyranoside ((+)-22). The addition of benzyl alcohol to isolevoglucosenone (3), followed by cross-aldol condensation with 3,6-[tert-butoxycarbonyl]imino-2,3,6-trideoxy-4,5-O-isopropylidene-L-ara bino-hexose ((+)-30) generated, after water elimination, a single enone ((+)-31) that was converted into a homo-(1-->3)-C-linked imino-disaccharide: 3-deoxy-3-(1',2',3',6'-tetradeoxy-3',6'-imino-L-arabino-hexitol-1'-C-yl) -beta-D-galactofuranose (44).

Official source

https://infoscience.epfl.ch/entities/publication/cced4667-5aae-41f5-bd01-7c7fa949d57d

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Pierre Vogel
2002
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/cced4667-5aae-41f5-bd01-7c7fa949d57d

About this result

Related concepts (4)

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.

Aldol condensation

An aldol condensation is a condensation reaction in organic chemistry in which two carbonyl moieties (of aldehydes or ketones) react to form a β-hydroxyaldehyde or β-hydroxyketone (an aldol reaction), and this is then followed by dehydration to give a conjugated enone. The overall reaction equation is as follows (where the Rs can be H) Aldol condensations are important in organic synthesis and biochemistry as ways to form carbon–carbon bonds.

Aldol reaction

The aldol reaction (aldol addition) is a reaction that combines two carbonyl compounds (aldehydes or ketones) to form a new β-hydroxy carbonyl compound. These products are known as aldols, from the aldehyde + alcohol, a structural motif seen in many of the products. The use of aldehyde in the name comes from its discovery history, where aldehydes were first used in the reaction and not ketones. Aldol structural units are found in many important molecules, whether naturally occurring or synthetic.