Biomimetic synthesis of enantiomerically pure D-myo-inositol derivatives

Chemical synthesis and functionalization of clickable glycosylphosphatidylinositol anchors

“…HPLC was also used in the synthesis of inositol 8 , although this may be mitigated by using enzymatic resolution 43 and exploring alternative routes such as de novo synthesis of PMB-protected inositols. 65 Finally, the moderate stereoselectivity obtained in the formation of pseudodisaccharide 31 , while consistent with our previous experience, may be improved by investigating recently published methods of stereoselective 1,2- cis -2-amino glycoside formation such as Nguyen’s Ni-catalyzed glycosylation. 66 Overall, PMB protection is comparable to benzyl protection in terms of efficiency, while offering an immense improvement in functional group tolerance.…”

Reactions of stereocontrolled intramolecular carbocyclization of levoglucosenone adduct with isoprene

“…In keeping with the spectral findings the stereochemical result of the transformation was analogous to that described in [12], namely, the acetate group is oriented equatorially, and the hydroxy group axially. The coupling constant between H 2 and H 3 equals 4.0 Hz, corresponding to the coupling constant of the cis-located protons.…”

Total Synthesis of Phosphatidylinositol Dimannoside: A Cell‐Envelope Component of Mycobacterium tuberculosis

“…[9] In these strategies, the optically pure myo-inositol derivatives with appropriate protecting groups are, however, obtained by multistep routes from d-glucose through Ferrier rearrangement [10] or by resolution from myo-inositol by using chiral auxiliaries in a 1:1 ratio. [11] To tackle these problems, we report herein a straightforward synthesis of PIM 2 1, a basic molecule toward the preparation of higher PIMs, LM, and LAM, employing direct 6-O-mannosylation of the myo-inositol-derived meso-4,6-diol as a key step.…”