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Synthesis of ceramide analogues (2S,3R)-96. Reagents and conditions: a) NaBH4, ZnCl2, MeOH, −78 °C, 0.5 h; b) LiAlH4, THF, rt, 3 h; c) TBDMSCl, DMAP, CH2Cl2, rt, 17 h; d) AcOH, CH2Cl2, rt, 10 h; e) KOH, EtOH, rt, 1 h; f) CDI, DBU, CH2Cl2, rt, overnight; g) Li, NH3 liquid, t-BuOH, THF, −78 °C, 0.5 h; h) RCOCl, NaHMDS, THF, −78 °C; i) TBAF, THF, 0 °C, 4 h.
