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An efficient route to 3-deoxy-d-manno-2-octulosonic acid (KDO) derivatives via a 1,4-cyclic sulfate approach

✍ Scribed by P.A.M. van der Klein; G.J.P.H. Boons; G.H. Veeneman; G.A. van der Marel; J.H. van Boom

Publisher: Elsevier Science
Year: 1989
Tongue: French
Weight: 247 KB
Volume: 30
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)80598-0

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✦ Synopsis

Treatment of 2,3:5,6-di-0-isopropylidene-D-mannitol with thionyl chloride followed by oxidation gave the corresponding 1,4-cyclic sulfate. Ring opening of the cyclic sulfate with the anion of ethyl 1,3-dithiane-2-carboxylate, and subsequent acidolysis and unmasking of the thioketal, afforded ethyl 4,5:7,8-di-O-isopropylidene-3-deoxy-a(8)-D-manno-2-octulosonate in an excellent yield.

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