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. Author manuscript; available in PMC: 2012 Dec 1.
Published in final edited form as: Medchemcomm. 2011 Oct 19;2(12):1167–1173. doi: 10.1039/C1MD00206F

Scheme 1.

Scheme 1

Preparation of C16:0, C16:1 phosphonoglycerol 1. Preparation of C16:0, C16:1-diether phosphonoglycerol 1 from dimethyl 3,4-bis (benzoyloxy)butylphosphonate 2: a) 2.2 equiv. TMSBr, CH2Cl2, −40 °C-rt; b) (COOH)2, cat. DMF, CH2Cl2, rt; c) rac-2-([9Z]-9-hexadecen-1-yloxy)-3-(hexadecyloxy)-propanol (5), Et3N, CHCl3, 76% over 3 steps; d) K2CO3, CH2Cl2/MeOH, 48 h, rt, 48%.