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Title: One-pot synthesis of carbohydrate thionolactones from 1-thiosugars
Contributor(s): Wilkinson, Brendan  (author)orcid ; Fairbanks, Antony J (author)
Publication Date: 2008
DOI: 10.1016/j.tetlet.2008.05.145
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Abstract: 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.
Publication Type: Journal Article
Source of Publication: Tetrahedron Letters, 49(33), p. 4941-4943
Publisher: Pergamon Press
Place of Publication: United Kingdom
ISSN: 0040-4039
Field of Research (FOR): 030503 Organic Chemical Synthesis
Socio-Economic Outcome Codes: 970103 Expanding Knowledge in the Chemical Sciences
Peer Reviewed: Yes
HERDC Category Description: C1 Refereed Article in a Scholarly Journal
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Appears in Collections:Journal Article
School of Science and Technology

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