Chiral Deuteration at C-6 of 1,6-Anhydrohexose Derivatives
- 6 December 1986
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 5 (4) , 585-600
- https://doi.org/10.1080/07328308608062977
Abstract
Photobromination and the succeeding deuteration with tri-n-butyltindeuteride were performed on eight 1,6-anhydro-2,3,4-tri-O-benzoylhexopyranoses to give C-6 chirally deuterated hexopyranoses. The stereochemistry of these two reactions are discussed in terms of steric effects of substituents at C-2, C-3 and C-4 of 1,6-anhydrohexopyranoses.This publication has 18 references indexed in Scilit:
- Stereochemistry of ribostamycin biosynthesis. Application of hydrogen-2 NMR spectroscopyJournal of the American Chemical Society, 1981
- Photo-bromination of carbohydrate derivatives. Part 3. C-5 bromination of penta-O-benzoyl-α- and -β-D-glucopyranose; a route toD-xylo-hexos-5-ulose derivatives and α-L-idopyranosidesJournal of the Chemical Society, Perkin Transactions 1, 1980
- Stereochemistry of Dehydrogenation by D-Galactose OxidaseCanadian Journal of Chemistry, 1971
- Crystalline modifications of 1,6-anhydro-β-d-altropyranose, and two strongly levorotatory esters thereofCarbohydrate Research, 1969
- NMR‐Spektren von 1.6‐Anhydro‐β‐D‐hexopyranosenEuropean Journal of Organic Chemistry, 1968
- Carboxoniumverbindungen in der Kohlenhydratchemie, III. Einfache Synthese von D‐Idose aus D‐Glucose durch mehrfache Acetoxonium‐Ion‐Umlagerungen. Darstellung eines stabilen Acetoxonium‐Salzes der Tetraacetyl‐idoseEuropean Journal of Inorganic Chemistry, 1967
- Deuterium Isotope Effect in Proton Nuclear Resonance SpectroscopyThe Journal of Chemical Physics, 1958
- Transformation of D-Gulose to 1,6-Anhydro-β-D-gulopyranose in Acid Solution1,2Journal of the American Chemical Society, 1955
- 341. Derivatives of 1 : 6-anhydro-β-D-idoseJournal of the Chemical Society, 1949
- D-Mannosanβ or Levomannosan1Journal of the American Chemical Society, 1941