Investigations into the Chemistry of Some 1,6-Epithio and 1,6-Episeleno ß-D-Glucopyranoses
Derivatives of 1,6-dideoxy-1,6-epithio-β-D-glucopyranose have been shown to undergo oxidation reactions to afford the corresponding sulfoxides and sulfones. The sulfoxides participate in Pummerer reactions to afford the corresponding α-acetoxy sulfides which were then oxidized further. None of the sulfoxides, sulfones or α-acetoxy sulfides prepared were particularly efficient glycosyl donors. Also presented are crystal structures of 1,6-dideoxy-1,6-epithio-β-D-glucopyranose S,S-dioxide and 1,6-dideoxy-1,6-episeleno-β-D-glucopyranose, interesting analogues of 1,6-anhydro-β-D-glucopyranose.
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1975 ◽
Vol 31
(3)
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pp. 852-856
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2009 ◽
Vol 2009
(34)
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pp. 5227-5232
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1994 ◽
Vol 67
(1)
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pp. 222-226
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