57 research outputs found
Rapid Synthesis of L-Idosyl Glycosyl Donors from α- Thioglucosides for the Preparation of Heparin Disaccharides
A new methodology for the synthesis of the most
challenging heparin building block has been developed.
Orthogonally protected L-idosyl glycosyl donors were prepared by
C5 epimerization of the corresponding thioglucosides using the
hydroboration/oxidation method followed by a 4,6-acetal formation.
The -anomeric configuration was crucial and the bulky C4
substituent was advantageous for the high L-ido diastereoselectivity.
The 4,6-arylmethylene group proved to be a directing element in
glycosylation thereby stereoselective -idosylation could be
achieved by using idosyl donors without a C-2 participating group
ChemInform Abstract: Synthesis of C-Glycosylacetylenes: Applications to the 2-Azidosugars.
ChemInform Abstract: Novel para-Substituted Benzyl Ethers for Hydroxyl Group Protection.
Does a chiral alcohol really racemize when its OH group is protected with Boyer's reaction?
Oligosaccharide Analogues of Polysaccharides. Part 7. Synthesis of a monosaccharide-derived monomer for amylose and cyclodextrin analogues
Multigram syntheses of the disaccharide repeating units of chondroitin 4- and 6-sulfates
- …