Publication

Total Asymmetric-Synthesis of 3-Deoxy-Hexoses and 4-Deoxy-Hexoses and Derivatives

Pierre Vogel
1992
Journal Articles

Abstract

(1S,4S)-7-Oxabicyclo[2.2.1]hept-5-en-2-one ((-)-5, a "naked sugar") has been converted to (-)-(1R,4S,6S)-6-endo-benzyloxy-2-bromo-7-oxabicyclo[2.2.1]hept-2-ene ((-)-12) in a highly stereoselective fashion. Double hydroxylation of the C=C double bond of (-)-12, followed by acetylation and Baeyer-Villiger oxidation of the resulting alpha-acetoxyketone (-)-14 afforded (-)-5-O-acetyl-2-O-benzyl-3-deoxy-beta-D-arabino-hexofuranurono-6,1-lact one ((-)-15). This compound was converted readily into (+)-methyl 3-deoxy-alpha-D-arabino-hexofuranoside ((+)-6) and (+)-methyl 3-deoxy-beta-L-xylo-hexofuranoside ((+)-7) and partially protected derivatives. (-)-15 was also converted into 4-deoxy-D-lyxo-hexopyranose (34) and several partially protected derivatives such as (+)-methyl 4-deoxy-2,3-O-isopropylidene-alpha-D-lyxo-hexo-pyranoside ((+)-8).

Official source

https://infoscience.epfl.ch/entities/publication/8000cdeb-e46e-4f20-80db-41382c4329ab

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Pierre Vogel
1992
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/8000cdeb-e46e-4f20-80db-41382c4329ab

About this result

Related concepts (4)

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.

Asymmetric induction

Asymmetric induction (also enantioinduction) describes the preferential formation in a chemical reaction of one enantiomer or diastereoisomer over the other as a result of the influence of a chiral feature present in the substrate, reagent, catalyst or environment. Asymmetric induction is a key element in asymmetric synthesis. Asymmetric induction was introduced by Hermann Emil Fischer based on his work on carbohydrates. Several types of induction exist.

Pyrrole

Pyrrole is a heterocyclic, aromatic, organic compound, a five-membered ring with the formula . It is a colorless volatile liquid that darkens readily upon exposure to air. Substituted derivatives are also called pyrroles, e.g., N-methylpyrrole, . Porphobilinogen, a trisubstituted pyrrole, is the biosynthetic precursor to many natural products such as heme. Pyrroles are components of more complex macrocycles, including the porphyrinogens and products derived therefrom, including porphyrins of heme, the chlorins, bacteriochlorins, and chlorophylls.