Stereoselective synthesis of thioxylooligosaccharides from S-glycosyl isothiourea precursors

A stereoselective synthesis of thioxylo-di-, -tri-, -tetra- and -penta-saccharides from S-glycosyl isothiourea precursors is described. The synthesis was performed starting from 2,3,4-tri- O-acetyl-β- d-xylopyranosyl isothiouronium bromide using a triethylamine promoted reaction with 1,2,3-tri- O-be...

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Bibliographic Details
Published in:Tetrahedron letters 2001-07, Vol.42 (27), p.4565-4567
Main Authors: Ibatullin, Farid M, Shabalin, Konstantin A, Jänis, Janne V, Selivanov, Stanislav I
Format: Article
Language:English
Subjects:
S-glycosyl isothiourea derivatives
thiooligosaccharides
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Summary:A stereoselective synthesis of thioxylo-di-, -tri-, -tetra- and -penta-saccharides from S-glycosyl isothiourea precursors is described. The synthesis was performed starting from 2,3,4-tri- O-acetyl-β- d-xylopyranosyl isothiouronium bromide using a triethylamine promoted reaction with 1,2,3-tri- O-benzoyl-4- O-trifluoromethanesulphonyl-β- l-arabinopyranose. The resulting 4-thioxylobiose was then converted into the corresponding isothiouronium bromide and used for the synthesis of 4,4′-dithioxylotriose. Higher homologues of the series and their α-methyl glycosides were also prepared. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(01)00775-4