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Bioorg Med Chem Lett. 2014 Jun 15;24(12):2777-80. doi: 10.1016/j.bmcl.2014.03.069. Epub 2014 Apr 1.

Concise synthesis of C-1-cyano-iminosugars via a new Staudinger/aza Wittig/Strecker multicomponent reaction strategy.

Author information

1
Glycogroup, Institute of Organic Chemistry, Technical University Graz, Stremayrgasse 9, A-8010 Graz, Austria.
2
Institute of Inorganic Chemistry, Technical University Graz, Stremayrgasse 9, A-8010 Graz, Austria.
3
Department of Chemistry, 2036 Main Mall, University of British Columbia, Vancouver, B.C. V6T 1Z1, Canada.
4
Laboratoire de Glycochimie, des Antimicrobiens et des Agroressources, CNRS-FRE 3517, Université de Picardie Jules Verne, 33 Rue St Leu, 80039 Amiens, France.
5
Laboratoire de Glycochimie, des Antimicrobiens et des Agroressources, CNRS-FRE 3517, Université de Picardie Jules Verne, 33 Rue St Leu, 80039 Amiens, France. Electronic address: aloysius.siriwardena@u-picardie.fr.
6
Glycogroup, Institute of Organic Chemistry, Technical University Graz, Stremayrgasse 9, A-8010 Graz, Austria. Electronic address: t.wrodnigg@tugraz.at.

Abstract

A new Staudinger/aza Wittig/Strecker multicomponent reaction sequence to C-1-cyano iminoalditols has been developed. When applied to 5-azidodeoxy-d-xylose and -d-glucose as substrates the method leads smoothly in good yield and with excellent stereoselectivity to respectively, 1,5-dideoxy-1,5-imino-d-idurono nitrile and 2,6-didesoxy-2,6-imino-d-glycero-d-ido-heptononitrile.

KEYWORDS:

C-1-cyano-iminosugar building blocks; Glucocerebrosidase; Glycosidase inhibitor; Iminoalditol; Staudinger/aza Wittig Strecker multicomponent reaction

PMID:
24803362
DOI:
10.1016/j.bmcl.2014.03.069
[Indexed for MEDLINE]

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