Enantioseparation in the synthesis of myo-inositol phosphates by high-performance liquid chromatography using a β-cyclodextrin-bonded column

Regioselective Protection and Deprotection of Inositol Hydroxyl Groups

“…Although enzymatic methods of resolution of myo -inositol derivatives have contributed much to the total synthesis of inositol phosphates and related lipids, further investigation is necessary to understand and explain the regioselectivities and enantioselectivities observed. A valuable alternative to chemical or enzyme-mediated resolution of inositol derivatives is the direct chromatography of enantiomers, but this technique has not yet been explored sufficiently. 28d,110b, …”

Membrane-Permeant 3-OH-Phosphorylated Phosphoinositide Derivatives

“…Phosphitylation of rac ‐ 10 and subsequent oxidation of the phosphoric triester8 resulted in the fully protected inositol 3,5‐bisphosphate derivative rac ‐ 12 . The enantiomers were separated by preparative chiral HPLC (50×250 mm, Chiradex, Merck)9 and furnished the alcohols 13 and ent ‐ 13 after cleavage of the silyl groups by treatment with triethylamine trihydrofluoride.…”

Membranpermeable 3-OH-phosphorylierte Phosphoinositidderivate

“…Phosphitylierung von rac ‐ 10 und anschließende Oxidation der Phosphorigsäuretriester8 lieferte das vollständig geschützte Inosit‐3,5‐bisphosphatderivat rac ‐ 12. Die Enantiomere wurden mittels präparativer HPLC an chiraler Phase (50×250 mm, Chiradex, Merck) getrennt 9. Die anschließende Abspaltung der Silylschutzgruppe mit Triethylamintrihydrofluorid führte zu den Alkoholen 13 und ent ‐ 13 .…”