A de novo approach to C-branched inositols: synthesis of a myo-inositol precursor for C-linked glycosyl phosphatidylinositols.
C-Linked glycosyl inositols are valuable structure-activity probes because of their greater hydrolytic stability and different conformational behavior compared with their parent O-glycosides. Simple C-branched inositols are synthetic precursors to these and other groups of inositol mimetics. Herein is described a de novo synthesis of C-branched inositols that contain a versatile ethenyl side chain for elaboration into more complex appendages. The approach centers on a stereoselective oxocarbenium ion-allylsilane cyclization and provides C-branched inositols with different stereochemical motifs. The synthesis of C-ethenyl-di-O-isopropylidene-myo-, neo-, epi-, and allo-inositols is discussed.
Hans
Sunej
S
Department of Chemistry, Hunter College, 695 Park Avenue, New York, NY 10021, USA.
Mootoo
David R
DR
D002236:Carbohydrate Conformation; D017261:Glycosylphosphatidylinositols / Q000138:chemical synthesis*; D007294:Inositol / Q000031:analogs & derivatives / Q000138:chemical synthesis
D017261:Glycosylphosphatidylinositols; D007294:Inositol