Synthesis of methyl beta-D-arabinofuranoside 5-[1D (and L)-myo-inositol 1-phosphate], the capping motif of the lipoarabinomannan of Mycobacterium smegmatis.

The total synthesis of methyl beta-D-arabinofuranoside 5-(myo-inositol 1-phosphate), the capping motif of the lipoarabinomannan (LAM) of Mycobacterium smegmatis, has been completed. The stereoselective synthesis of beta-D-arabinofuranosides has been achieved via an internal aglycon delivery approach using Ogawa and Ito's method. Coupling with enantiomeric myo-inositol derivatives gave the diastereoisomeric title compounds in good overall yield. Comparison with the natural product firmly established the proposed structure for the capping of the LAM but left the absolute configuration of the myo-inosityl moiety undetermined.