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Synlett 1990; 1990(6): 311-313
DOI: 10.1055/s-1990-21073
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Iodonium Ion Promoted Cyclization: A Convenient Approach to Glycosyl Donors of 3-Deoxy-D-manno-2-octulosonic Acid (KDO)

Pieter A. M. van der Klein* , Gerrt J. P. H. Boons, Gerrit H. Veeneman, Gijs A. van der Marel, Jacques H. van Boom
  • *Gorlaeus Laboratories, P.O. Box 9502, NL-2300 RA Leiden, The Netherlands
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Publication Date:
08 March 2002 (online)

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Cyclization of methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-D-manno-octulonate diethyl dithioacetal with iodonium sym-dicollidine perchlorate or N-iodosuccinimide yields methyl 2,3-dideoxy-4,5:7,8-di-O-isopropylidene-D-manno-oct-2-enulosonate (KDO-glycal) or the ethyl 2-thio-α-glycoside of 3-deoxy-D-manno-2-octulosonic acid, respectively. The latter compounds can be employed as glycosyl donors of 3-deoxy-D-manno-2-octulosonic acid.

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