Synthesis of Mycobacterium tuberculosis Sulfolipid-3 Analogues and Total Synthesis of the Tetraacylated Trehaloglycolipid of Mycobacterium paraffinicum

A novel methodology for the regioselective O6 acylation of the 2,3-diaryl trehaloses to access Mycobacterium tuberculosis sulfolipid SL-3 and related 2,3,6-triester glycolipid analogues is reported for the first time. The methodology was successfully extended to achieve the first total synthesis of the tetraacylated trehalose glycolipid from Mycobacterium paraffinicum. The corresponding 2,3,6'-triesters trehalose glycolipids were also synthesized starting from the common 2,3-diacyl trehalose. These synthetic glycolipids are potential candidates for serodiagnosis and vaccine development for tuberculosis.