Anomeric activation of thioglycosides and preparation of deoxyglycosides using polymer-bound iodate(I) complexes

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OriginalspracheEnglisch
Seiten (von - bis)637-639
Seitenumfang3
FachzeitschriftTetrahedron Letters
Jahrgang44
Ausgabenummer4
PublikationsstatusVeröffentlicht - 20 Jan. 2003

Abstract

New thiophilic polymer-bound haloate(I) complexes are presented which are well suited for the polymer-assisted solution-phase activation of 2-deoxythioglycosides. In the presence of alcohols 2-deoxyglycosides are obtained in yields between 60 and 95%. Isolation of the target glycosides is further simplified by removing the byproduct diphenyldisulfide by reductive work-up. Here also a polymer-bound reagent, namely borohydride exchange resin, served as a tool for sequestering the sulfur-containing impurities.

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Anomeric activation of thioglycosides and preparation of deoxyglycosides using polymer-bound iodate(I) complexes. / Jaunzems, Janis; Sourkouni-Argirusi, Georgia; Jesberger, Martin et al.
in: Tetrahedron Letters, Jahrgang 44, Nr. 4, 20.01.2003, S. 637-639.

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

Jaunzems J, Sourkouni-Argirusi G, Jesberger M, Kirschning A. Anomeric activation of thioglycosides and preparation of deoxyglycosides using polymer-bound iodate(I) complexes. Tetrahedron Letters. 2003 Jan 20;44(4):637-639. doi: 10.1016/S0040-4039(02)02708-9
Jaunzems, Janis ; Sourkouni-Argirusi, Georgia ; Jesberger, Martin et al. / Anomeric activation of thioglycosides and preparation of deoxyglycosides using polymer-bound iodate(I) complexes. in: Tetrahedron Letters. 2003 ; Jahrgang 44, Nr. 4. S. 637-639.
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T1 - Anomeric activation of thioglycosides and preparation of deoxyglycosides using polymer-bound iodate(I) complexes

AU - Jaunzems, Janis

AU - Sourkouni-Argirusi, Georgia

AU - Jesberger, Martin

AU - Kirschning, Andreas

PY - 2003/1/20

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AB - New thiophilic polymer-bound haloate(I) complexes are presented which are well suited for the polymer-assisted solution-phase activation of 2-deoxythioglycosides. In the presence of alcohols 2-deoxyglycosides are obtained in yields between 60 and 95%. Isolation of the target glycosides is further simplified by removing the byproduct diphenyldisulfide by reductive work-up. Here also a polymer-bound reagent, namely borohydride exchange resin, served as a tool for sequestering the sulfur-containing impurities.

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JO - Tetrahedron Letters

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