Synthesis and Structural Characterization of Three Unique Helicobacter pylori α‐Cholesteryl Phosphatidyl Glucosides

摘要: Steryl glycosides produced by bacteria play important biological roles in the evasion and modulation of host immunity. Step-economical syntheses three cholesteryl-6-O-phosphatidyl-α-D-glucopyranosides (αCPG) unique to Helicobacter pylori have been achieved. The approach relies upon regioselective deprotection per-O-trimethylsilyl-α-D-cholesterylglucoside at C6 followed phosphoramidite coupling. Global TMS ether presence oxygen subsequent cyano ethyl phosphoester afforded target compounds 16–21 % overall yield starting from D-glucose. structures these natural products were determined using a combination 2D NMR methods mass spectrometry. These robust synthesis characterization protocols provide analogues facilitate glycolipidomic profiling studies.