Scheme 2. Synthesis of the Intermediate TEAHP (8) with the Opposite Conformation from the Native Glycerol Backbone.

Reagents and conditions: (a) 2,2-dimethoxypropane, HClO₄ and acetone at rt for 2 h, 92%; (b) LiAlH₄ and Et₂O at 0 °C, 94%; (c) TrCl, NEt₃, TBAI, and CH₂Cl₂ at rt for 2 h, 86%; (d) SbCl₃, H₂O, and CH₃CN under reflux for 4 h, 53%; (e) oleic acid, DCC, DMAP, and CH₂Cl₂ at 0 °C to rt, 96%; (f) TFA and CH₂Cl₂ at 0 °C for 0.5 h, 98%; (g) diphenyl phosphite and pyridine for 0.5 h then NEt₃/H₂O (1:1) for 1 h at rt, 92%.