Recognition of specific oxidized phospholipids oxPCCD36 by scavenger receptors CD36 and SR-BI plays a critical role in several pathophysiological processes. The structural basis for the recognition of oxPCCD36 by CD36 and SR-BI is poorly understood. We describe here the design and synthesis of a series of model oxidized phospholipids having various functional groups at sn-1, sn-2, and sn-3 positions. Synthetic methodologies and experimental details for the preparation of specific examples of model oxidized phospholipids are presented. The correlation between their structure and their ability to serve as ligands for CD36 and SR-BI was determined using competitive binding assay on cells overexpressing scavenger receptors, direct binding assay to scavenger receptors expressed as GST-fusion proteins, and cholesterol ester synthesis assay using mouse peritoneal macrophages.