An expeditious synthesis of a C-disaccharide using a temporary silaketal connection
- 1 January 1993
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 10,p. 864-865
- https://doi.org/10.1039/c39930000864
Abstract
Methyl α-C-maltoside 6 is expeditiously synthesized by radical coupling of the phenyl Se-glycoside 1 onto the exo-methylene sugar 2, which are temporarily connected through a silaketal tether.Keywords
This publication has 15 references indexed in Scilit:
- Synthesis and conformational studies of .beta.-(1.fwdarw.6)- and .beta.,.beta.-(1.fwdarw.1)-linked C-disaccharidesThe Journal of Organic Chemistry, 1993
- Enantiomerically pure 7-oxabicyclo[2.2.1]hept-5-en-2-yl derivatives (naked sugars) as synthetic intermediates. 18. Synthesis of .alpha.-(1.fwdarw.2)-, .alpha.-(1.fwdarw.3)-, .alpha.-(1.fwdarw.4)-, and .alpha.-(1.fwdarw.5)-C-linked disaccharides through 2,3,4,6-tetra-O-acetylglucopyranosyl radical additions to 3-methylidene-7-oxabicyclo[2.2.1]heptan-2-one derivativesThe Journal of Organic Chemistry, 1992
- Silicon-mediated reductive coupling of aldehydes and allylic alcohols. A stereoselective synthesis of tunicaminyluracilJournal of the American Chemical Society, 1991
- The temporary silicon connection method in the control of regio- and stereochemistry. Applications to radical-mediated reactions. The stereospecific synthesis of C-glycosidesJournal of the American Chemical Society, 1991
- Silaketals as tethers in intramolecular radical cyclisationsTetrahedron Letters, 1991
- Synthesis of methylene bridged C-disaccharidesTetrahedron Letters, 1988
- Synthesis of “C‐Disaccharides” by Radical C-C Bond FormationAngewandte Chemie International Edition in English, 1986
- Diastereoselective Syntheses of C‐GlycopyranosidesAngewandte Chemie International Edition in English, 1983
- Applications of radical addition reactions to the synthesis of a C-glucoside and a functionalised amino-acidJournal of the Chemical Society, Chemical Communications, 1983
- The first synthesis of a ‘C-disaccharide’Journal of the Chemical Society, Chemical Communications, 1983