Journal
TETRAHEDRON LETTERS
Volume 49, Issue 33, Pages 4941-4943Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.05.145
Keywords
carbohydrates; 1-thio sugars; thiocarbonyl compounds; thiosulfinates
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Funding
- EPSRC [EP/D051495/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/D051495/1] Funding Source: researchfish
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A general and efficient one-pot method for the synthesis of carbohydrate thionolactones from the corresponding 1-thiosugar is described involving the formation of an intermediate glycosyl S-tert-butyl thiosulfinate in situ by treatment of a thiol with commercially available tert-butylsulfinyl chloride in toluene at room temperature, followed by thermolysis. The method can also be used to generate reactive thioaldehydes and thioketones directly from thiols, which can be trapped in situ with a suitable diene. (C) 2008 Elsevier Ltd. All rights reserved.
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