1233506-63-2Relevant academic research and scientific papers
Asymmetric synthesis of d - Ribo -phytosphingosine from 1-tetradecyne and (4-Methoxyphenoxy)acetaldehyde
Liu, Zheng,Byun, Hoe-Sup,Bittman, Robert
, p. 4356 - 4364 (2010)
(Figure presented) 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 NaN3/NH4Cl. 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 α-galactosylceramide derivatives, was also readily prepared by this route.
