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. Author manuscript; available in PMC: 2013 Jun 1.
Published in final edited form as: Eur J Med Chem. 2012 Mar 16;52:159–172. doi: 10.1016/j.ejmech.2012.03.013

Scheme 3.

Scheme 3

Synthesis of Type II ortho ester lipids 4 and 5. Reagents and conditions: (a) pyridine/triflic anhydride/CH2Cl2, rt for 1.5 h, 100%; (b) HCOOH/HCHO/H2O, 0 to 65 °C, 10 h, 59%; (c) LDA/THF, -15 to -20 °C for 30 min; 6/THF, -15 to -20 °C for 30 min, rt for 1 h, 54%; (d) oleyl alcohol, NaH, THF, rt for 30 min; α,α-dichloromethyl methyl ether, 45 °C for 10 h, 20%; (e) CH3I, Na2CO3, THF, rt for 8 h, 100%, (f) Bio-Rex 5 resin (chloride form), CH2Cl2/MeOH, rt, 99%.