Publication

Stereoselective synthesis of alpha-C-galactopyranosides of conduritols and aminoconduritols

Pierre Vogel
1996
Journal Articles

Abstract

Giese's radical glycosidation of (-)-(1S,4R,5R,6R)-5-exo-(benzeneselenyl)-6-endo-chloro-3-methylidene-7-o xabicyclo[2.2.1]-heptan-2-one with tetra-O-acetylbromo-alpha-D-galactopyranose gave a C-galactoside that was converted into (+)-(1S,2R,3S,4R)-6-chloro-3,3-endo-[(2',3',4',6'-tetra-O-acetyl-alpha-D -galactopyranosyl)methyl]-7-oxa-bicyclo[2.2.1]hept-5-en-2-endo-yl acetate ((+)-6). Treatment of (+)-6 with HBr, then with LiN3 and subsequent reduction afforded (3S,4R,5R,6S)-3-amino-1-chloro-4-[(alpha-D-galactopyranosyl)methyl]-cycl ohex-1-en-5,6-diol ((+)-10). Acidic hydrolysis of (+)-6 provided the (3R,4R,5R,6S)-1-chloro-4-[(alpha-D-galactopyranosyl)methyl]-cyclohex-hex -1-en-3,5,6-triol derivative (+)-11 or the (4R,5R,6S)-4-[(alpha-D-galactopyranosyl)methyl]-5,6-dihydroxycyclohex-2- en-1-one derivative (-)-12 selectively.

Official source

https://infoscience.epfl.ch/entities/publication/b95ce81c-7b81-4f6d-9776-f134ecdaa361

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Pierre Vogel
1996
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/b95ce81c-7b81-4f6d-9776-f134ecdaa361

About this result

Related concepts (6)

X-gal

X-gal (also abbreviated BCIG for 5-bromo-4-chloro-3-indolyl-β--galactopyranoside) is an organic compound consisting of galactose linked to a substituted indole. The compound was synthesized by Jerome Horwitz and collaborators in 1964. The formal chemical name is often shortened to less accurate but also less cumbersome phrases such as bromochloroindoxyl galactoside. The X from indoxyl may be the source of the X in the X-gal contraction.

Β-Galactosidase

β-Galactosidase (EC 3.2.1.23, lactase, beta-gal or β-gal; systematic name β-D-galactoside galactohydrolase), is a glycoside hydrolase enzyme that catalyzes hydrolysis of terminal non-reducing β-D-galactose residues in β-D-galactosides. β-Galactosides include carbohydrates containing galactose where the glycosidic bond lies above the galactose molecule. Substrates of different β-galactosidases include ganglioside GM1, lactosylceramides, lactose, and various glycoproteins.

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.