Synthesis 2011(6): 867-872  
DOI: 10.1055/s-0030-1258437
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Practical and Cost-Effective Synthesis of d-erythro-Sphingosine from d-ribo-Phytosphingosine via a Cyclic Sulfate Intermediate

Yun Mi Lee, Seokwoo Lee, Hongjun Jeon, Dong Jae Baek, Jae Hong Seo, Deukjoon Kim, Sanghee Kim*
College of Pharmacy, Seoul National University, San 56-1, Shilim, Kwanak, Seoul 151-742, Korea
Fax: +82(2)8880649; e-Mail: pennkim@snu.ac.kr;
Further Information

Publication History

Received 4 January 2011
Publication Date:
10 February 2011 (online)

Abstract

The practical and efficient synthesis of d-erythro-sphingosine from commercially available d-ribo-phytosphingosine is described­. An important feature of this synthesis is the selective transformation of the 3,4-vicinal diol of phytosphingosine into the characteristic E-allylic alcohol of sphingosine via a cyclic sulfate intermediate that contains a non-nucleophilic trifluoroacetamide protecting group.

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4

Phytosphingosine from fermentation can be purchased at low cost direct from suppliers such as Cosmoferm B. V. and Doosan Biotech BU.

16

Owing to the reported instability of 1, it was also characterized as the triacetate derivative 11.