117487-48-6Relevant academic research and scientific papers
A concise and scalable synthesis of high enantiopurity (-)-d-erythro- sphingosine using peptidyl thiol ester-boronic acid cross-coupling
Yang, Hao,Liebeskind, Lanny S.
, p. 2993 - 2995 (2008/02/09)
A short and efficient synthesis of high enantiopurity (-)-D-erythro- sphingosine has been achieved in 71% yield over 6 steps from N-BOC-L-serine. The key steps are high yield, racemization-free, palladium-catalyzed, copper(I)-mediated coupling of the thiophenyl ester of N-Boc-O-TBS L-serine with E-1-pentadecenyl boronic acid and the highly diastereoselective reduction of the resulting peptidyl ketone with LiAI(O-t-Bu)3H. By using this concise route (-)-D-erythro-sphingosine can be prepared on large scale and in high enantio- and diastereopurity (ee >99%, de up to 99%).
