Publication

Enantiomerically Pure 7-Oxabicyclo[2.2.1]Hept-5-En-2-Yl Derivatives as Synthetic Intermediates .16. Total Asymmetric-Synthesis of 6-Deoxy-5-C-Methyl-D-Ribo-Hexose Structure in Aqueous-Solution

Pierre Vogel
1991
Journal Articles

Abstract

(1R,2R,4R)-2-exo-Cyano-7-oxabicyclo[2.2.1]hept-5-en-2-yl (1S)-camphanate [1, Diels Alder adduct of furan to 1-cyanovinyl (1S)-camphanate, a ''naked sugar''] was transformed with high stereoselectivity into (1S,4S,5R,6R,7R)-6-exo,7-exo-(isopropylidenedioxy)-4-exo-methyl-2,8-diox abicyclo[3.2.1]octan-3-one [(-)-4] and (1S,5R,6R,7R)-6-exo,7-exo-(isopropylidenedioxy)-4,4-dimethyl 2,8-dioxabicyclo[3.2.1] octan-3-one [(-)-51. Reaction of (-0-5 with Me3SiCH2Li gave 5,7-dideoxy-5,5-dimethyl-2,3-)-isopropylidene-CD-ribo-heptofuranos-6-ulo se [(+)-8, which was then converted into 6-deoxy-5-C-methyl-D-ribo-hexose (10 steps from furan, 59% overall yield) and derivatives. N.m.r. studies established that branching of 6-deoXy-D-allose by a methyl group at C-5 favours the furanose versus the pyranose form of the carbohydrate in aqueous solution.

Official source

https://infoscience.epfl.ch/entities/publication/fdc2f40e-d040-4c9f-82a8-533b74969005

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Pierre Vogel
1991
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/fdc2f40e-d040-4c9f-82a8-533b74969005

About this result

Related concepts (18)

Hexose

In chemistry, a hexose is a monosaccharide (simple sugar) with six carbon atoms. The chemical formula for all hexoses is C6H12O6, and their molecular weight is 180.156 g/mol. Hexoses exist in two forms, open-chain or cyclic, that easily convert into each other in aqueous solutions. The open-chain form of a hexose, which usually is favored in solutions, has the general structure H–(CHOH)n−1–C(=O)–(CHOH)4−n–H, where n is 1, 2, or 3.

Enantioselective synthesis

Enantioselective synthesis, also called asymmetric synthesis, is a form of chemical synthesis. It is defined by IUPAC as "a chemical reaction (or reaction sequence) in which one or more new elements of chirality are formed in a substrate molecule and which produces the stereoisomeric (enantiomeric or diastereomeric) products in unequal amounts." Put more simply: it is the synthesis of a compound by a method that favors the formation of a specific enantiomer or diastereomer.

Pyranose

Pyranose is a collective term for saccharides that have a chemical structure that includes a six-membered ring consisting of five carbon atoms and one oxygen atom. There may be other carbons external to the ring. The name derives from its similarity to the oxygen heterocycle pyran, but the pyranose ring does not have double bonds. A pyranose in which the anomeric OH at C(l) has been converted into an OR group is called a pyranoside. The pyranose ring is formed by the reaction of the hydroxyl group on carbon 5 (C-5) of a sugar with the aldehyde at carbon 1.