A facile stereodivergent synthesis of threo- and erythro-N,N-dibenzyl sphingosines from (S)-N,N-dibenzyl-O-TBDMS-serinal

Add time:07/22/2019    Source:sciencedirect.com

The (L)-threo-N,N-dibenzyl sphingosine was prepared in two steps from the serinal derivative 1 by diastereoselective alkenylation with pentadec-1-enyl(ethyl)zinc and deblocking. (D)-erythro-N,N-Dibenzyl sphingosine was also prepared in two steps from 1 by a highly diastereoselective alkynylation with pentadecynyl magnesium bromide and subsequent stereoselective LAH reduction.

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