96026-75-4Relevant academic research and scientific papers
The UDP-Galp mutase catalyzed isomerization: Synthesis and evaluation of 1,4-anhydro-β-d-galactopyranose and its [2.2.2] methylene homologue
Sadeghi-Khomami, Ali,Forcada, Tatiana J.,Wilson, Claire,Sanders, David A. R.,Thomas, Neil R.
experimental part, p. 1596 - 1602 (2010/07/04)
The synthesis of 1,4-anhydro-β-d-galactopyranose (1,5-anhydro-α- d-galactofuranose), a proposed intermediate in the ring contraction isomerisation catalyzed by UDP-galactopyranose mutase, together with its [2.2.2] bicyclic methylene homologue, synthesised as a possible competitive inhibitor or alternative substrate, are reported. Neither compound was found to be an inhibitor or substrate for UDP-galactopyranose mutase from Klebsiella pneumoniae.
Glycosylations of tertiary alcohols: Synthesis of fully protected disaccharides with sterically demanding groups attached to the sugar core
Holkenbrink, Annika,Vicente, Jordi Bertran,Werz, Daniel B.
experimental part, p. 2596 - 2604 (2009/12/24)
Modified gluco- and galactopyranosides with sterically demanding groups in the 4-position were synthesized. Glycosylation studies of these tertiary alcohols with glycosyl trichloroacetimidates and glycosyl phosphates were performed. Despite steric hindran
Steric Effects Are Not the Cause of the Rate Difference in Hydrolysis of Stereoisomeric Glycosides
Jensen, Henrik Helligso,Bols, Mikael
, p. 3419 - 3421 (2007/10/03)
(Equation presented) A long-lived and plausible explanation as to why glycosides with axial substituents are more reactive than those with equatorial substituents was given in 1955 by Edward based on sterical hindrance being relieved in the transition state. Using model compounds 5, 6, 8, and 10, we here show conclusively that sterical hindrance not is the controlling factor in glycoside hydrolysis.
Spiroketal Synthesis. - A Case of Intramolecular Glycoside Bond Formation
Preuss, Rainer,Jung, Karl-Heinz,Schmidt, Richard R.
, p. 377 - 382 (2007/10/02)
From 4-O-unsubstituted glucose derivatives 1a, b the 4-hydroxymethyl-substituted glucose derivatives 9a, b were obtained via oxidation to the ketone, Wittig reaction with methylenetriphenylphosphorane, borane addition, and subsequent oxidation to yield th
