Synthesis of phosphatidylinositol mannosides (PIMs)

摘要

Two strategies towards the synthesis of phosphatidylinositol mannosides (PIMs) were elaborated which permit selective access to the O-1-,O-2-,and the O-6 position of the myo-inositol residue.Starting materials are 1,2:5,6,-and 1,2:4,5-di-O-cyclohexylidene-DL-myo-inositol,respectively.In the latter case,the required assignment to the D-or L-series is based on the transformation of one enantiomer into known (-)-liriodentritol.The efficiency and potential versatility of the two approaches is exemplified in the synthesis of PIMs (D)-1a and its pseudoenantiomer (L)-1b,both having myrostoyl residues as part of the phosphatidyl moiety.