Scheme 19.
Synthesis of sphingolipid analogues (R)-76. Reagents and conditions: a) BnBr, Mg, THF, reflux, 6 h; b) LiAlH4, THF, 0 °C, 1 h; c) MsCl, TEA, CH2Cl2, 0 °C, 1 h; d) LiAlH4; e) TMSCl, NaI, MeCN, rt, 2 h then pyrrolidine, reflux, 2 h; f) H2, Pd(OH)2, AcOH, EtOH, rt; g) RC(O)Cl, NaOH, THF/H2O, rt.