Synthesis of thiosaccharides employing the Pummerer rearrangement of tetrahydrothiopyran oxides

The Pummerer rearrangement of 1-deoxy-5-thioglucopyranose derivatives carrying acetonides at the C3,4-positions proceeded regioselectively at the C1 position by treating with TFAA in the presence of pyridine. Studies employing deuterium-labelled derivatives revealed that the reaction was induced by...

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Bibliographic Details
Published inTetrahedron Vol. 60; no. 32; pp. 6829 - 6851
Main Authors Fujita, Junji, Matsuda, Hiroko, Yamamoto, Kazunori, Morii, Yasuharu, Hashimoto, Masaru, Okuno, Toshikatsu, Hashimoto, Kimiko
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 02.08.2004
Elsevier
Subjects
Chemistry
Chemistry, Organic
Isomaltotriose analogue
Physical Sciences
Pummerer rearrangements
Reaction mechanism
Science & Technology
Thiosaccharids
Reaction mechanism
Thiosaccharids
Isomaltotriose analogue
Pummerer rearrangements
SELECTIVE GLYCOSYLATION
DISACCHARIDES
pummerer rearrangements
ALPHA-L-FUCOSIDASES
isomaltotriose analogue
METHYL
thiosaccharids
SULFUR
KETONES
5-THIOGLUCOPYRANOSE DERIVATIVES
reaction mechanism
STEREOSELECTIVE-SYNTHESIS
CONFORMATIONAL-ANALYSIS
INHIBITORS
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Summary:The Pummerer rearrangement of 1-deoxy-5-thioglucopyranose derivatives carrying acetonides at the C3,4-positions proceeded regioselectively at the C1 position by treating with TFAA in the presence of pyridine. Studies employing deuterium-labelled derivatives revealed that the reaction was induced by E2 1,2-elimination of trifluoroacetic acid of the trifluoroacetoxy sulfonium intermediate. This methodology was applied to the synthesis of an isomaltotriose derivative consisting of 5-thioglucopyranoside units. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.06.006