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Asymmetric synthesis of D-ribo-phytosphingosine from 1-tetradecyne and (4-methoxyphenoxy)acetaldehyde.

The Journal of organic chemistry (2010-06-10)
Zheng Liu, Hoe-Sup Byun, Robert Bittman
RÉSUMÉ

An asymmetric synthesis of d-ribo-phytosphingosine (1) was achieved by utilizing the ProPhenol (12)-catalyzed alkynylation of unsaturated aldehyde 8 to afford allylic propargylic alcohol (S)-6 followed by asymmetric epoxidation and opening of propargylic epoxy alcohol anti-5 with NaN(3)/NH(4)Cl. Deprotection and reduction of the resulting acyclic azide 3 then gave 1. Alkyne-azide 3 was subjected to an intramolecular click reaction, generating a bicyclic triazole, which was found to have unexpected vicinal coupling constants. Application of the advanced Mosher method verified the configurations of the three contiguous stereogenic centers of 1. An alkynyl azide analogue of 1, which may be useful as a glycosyl acceptor in the synthesis of alpha-galactosylceramide derivatives, was also readily prepared by this route.

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Avanti
N-24:0 Phytosphingosine, Avanti Research - A Croda Brand 860724P, powder
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Avanti
D-ribo-Phytosphingosine, Avanti Research - A Croda Brand 860499P, powder
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Avanti
D-ribo-phytosphingosine (C17 base), Avanti Research - A Croda Brand 860602P, powder
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Avanti
N-08:0 Phytosphingosine, Avanti Research - A Croda Brand 860609P, powder
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Avanti
N-16:0 Phytosphingosine, Avanti Research - A Croda Brand 860617P, powder
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