An Improved Method for the Regioselective Oxidation of Stannylene Acetals and Dimerization of the α-Hydroxyketone Products
- 1 June 1993
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 12 (4) , 557-571
- https://doi.org/10.1080/07328309308019407
Abstract
Dibutylstannylene acetals, particularly those derived from terminal diols, were found to be oxidized regiospeeifically to α-hydroxyketones in good to excellent yield by N-bromosuccinimide. One of the products, 3-deoxy-l,2-O-isopropylidene-α-D-erythro hexofuranos-5-ulose (8), exists to about 20% in solution as a mixture of dimers. One of the dimers can be obtained as a solid and its structure was determined tentatively by a combination of NMR experiments and MM3 molecular mechanics calculations.Keywords
This publication has 15 references indexed in Scilit:
- Pyrrolidine and piperidine aminosugars from dicarbonyl sugars in one step. Concise synthesis of 1-deoxynojirimycinTetrahedron Letters, 1990
- Chiral precursors for syntheses of furanoterpenesTetrahedron, 1989
- The regioselectivity of dibutylstannylene-mediated oxidation of methyl 3',4'-O-isopropylidene-α- and β-lactoside. A new synthesis of n -acetylllactosamineTetrahedron, 1987
- Regioselective oxidation of carbohydrate triols: facile synthesis of 2,3-O-isopropylidene-β-d-threo-hexo-2,4-diulo-pyranose and 1,2-O-isopropylidene-β-d-threo-hexo-2,5,diulo-pyranoseCarbohydrate Research, 1986
- Regioselective manipulation of hydroxyl groups via organotin derivativesTetrahedron, 1985
- The Isomeric Composition of 6-Deoxy-D- XYLO -Hexos-5-Ulose in Aqueous Solution as Determined by 1 H and 13 C NMRJournal of Carbohydrate Chemistry, 1983
- Synthesis of (+)-spectinomycinJournal of the American Chemical Society, 1979
- Dimeric nature of the aldehyde produced from methyl β-D-galactopyranoside by D-galactose oxidaseCarbohydrate Research, 1974
- The structure of dihydroxyacetone in solutionBioorganic Chemistry, 1973
- Chemical synthesis of D-xylo-hexos-5-ulose 6-phosphate, a putative intermediate in the biosynthesis of myo-inositolThe Journal of Organic Chemistry, 1968