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. Author manuscript; available in PMC: 2016 Mar 2.
Published in final edited form as: Mol Pharm. 2015 Jan 27;12(3):742–750. doi: 10.1021/mp500581r

Scheme 2. Preparation of Amphipathic Carbonate Co-oligomersa.

Scheme 2

a(A) Synthesis by ring-opening oligomerization, followed by guanidine deprotection. Reagents and conditions: (a) (i) R–OH, 7 (5 mol %), DBU (5 mol %), lipidated monomer 3 or 8, CH2Cl2, rt, (ii) guanidinylated monomer 6 or 9; (b) TFA, CH2Cl2, rt; yields (over 2 steps): 10 = 45%, 11 = 48%, 12 = 75%, 13 = 34%. (B) Co-oligomers were synthesized with one of two possible lipidated monomers and guanidine monomers. (C) Structures (X, Y) and DP (n, m) of co-oligomers. bFrom ref 21.