Stereoselective mono- and bis-homologation of L-serinal via 2-trimethylsilylthiazole addition. The thiazole route to amino L-sugars and D-erythro-sphingosines

Abstract

anti-Addition [92% diastereoselectivity (d.s.)] of 2-trimethylsilylthiazole (2) to O,N-protected L-serinal (1) and deblocking the formyl group in the resulting adduct, leads to the (2S,3S)-2,4-dihydroxy-3-aminobutanal derivative (7), which serves as a precursor both to masked 4-amino-4-deoxy-L-ribose/L-arabinose and D-erythro-C20-sphingosine.