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Synthesis 2010(17): 2979-2984
DOI: 10.1055/s-0029-1218844
DOI: 10.1055/s-0029-1218844
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Asymmetric Synthesis of the α-d-Galactosyl Ceramide KRN7000 via an Organocatalytic Aldol Reaction as Key Step
Further Information
Received
19 May 2010
Publication Date:
29 June 2010 (online)
Publication History
Publication Date:
29 June 2010 (online)
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Abstract
The asymmetric synthesis of the antitumor and immunostimulatory α-d-galactosyl ceramide KRN7000 using a (R)-proline-catalyzed enantioselective aldol reaction as key step is described. The title compound is synthesized in thirteen linear steps with excellent stereoselectivity (de >98%, ee = 95%) employing the commercially available substrates 1-pentadecanal, 2,2-dimethyl-1,3-dioxan-5-one, hexacosanoic acid, and d-galactose.
Key words
α-galactosyl ceramide - asymmetric synthesis - aldol reaction - organocatalysis - proline
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