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. Author manuscript; available in PMC: 2016 Feb 28.
Published in final edited form as: J Control Release. 2014 Dec 24;200:23–34. doi: 10.1016/j.jconrel.2014.12.028

Scheme 1.

Scheme 1

Synthesis of the amphiphilic macromolecular prodrug SIM-mPEG. a) PPh3 (5 eq), I2 (4 eq), DCM, RT, 24 h, 79.1%; b) NaN3 (20 eq), DMF, 100°C, 24h, 93.4%; c) 3-butyn-1-ol (6 eq), TsOH·H2O (0.1 eq), RT, 3h, 30.3%; d) succinic anhydride (6eq), Et3N (4 eq), DMAP (0.4 eq), 45°C, 20 h, 94.6%; e) DCC (2.5 eq), SIM (2.5 eq), DMAP (0.06 eq), 0°C, 1.5 h, 58.6%; f) 6 (2.5 eq), 3 (1 eq), CuSO4·5H2O (1 eq), L-ascorbic acid sodium salt (2 eq), t-BuOH/H2O, 60 h, 77.3%.