Enzyme assisted synthesis of enantiomerically pure myo-inositol derivatives - chiral building blocks for inositol polyphosphates

Chelation controlled regiospecific O-substitution of myo-inositol orthoesters: convenient access to orthogonally protected myo-inositol derivatives

“…10 These variations were utilized to obtain either mono-O-substituted derivatives (6-12, Scheme 1) or di-Osubstituted derivatives (13-16) in poor to good isolated yields. O-Alkylation 7 and O-acylation 8 of myo-inositol orthoesters 1 and 2 in the presence of sodium hydride are particularly interesting due to the very high regioselectivity observed, which was thought to be due to the involvement of chelates such as 4.…”

Experimental design of the kinetic resolution of a key precursor of high‐value bioactive myo‐inositols by an immobilized lipase

“…Cromatographic determinations of the enantiomeric excesses ( ee ) of L‐(−)‐ 2 were done on the same equipment mentioned above carrying a Chiralcel OD‐H column (5 µm; 4.6 × 250 mm), eluted with 9:1 hexane:2‐propanol (0.8 mL min −1 ). The retention times of the enantiomers: (D)‐ 2 (15.7 min), (L)‐ 2 (22.3 min) . The enantiomeric ratio (E) was calculated using the equation of Chen et al …”

“…This makes the syntheses longer and low‐yielding . At the outset of our investigations on novel substrates, only few reports had involved kinetic resolutions or desymmetrizations by lipase, despite the clear advantages of the use of these biocatalysts over the cumbersome derivatization protocols …”

Regioselectivity among six secondary hydroxyl groups: selective acylation of the least reactive hydroxyl groups of inositol

“…Treatment of myo-inositol with trialkylorthoesters in presence of acid catalysts such as PTSA, 5 Camphorsulfonic acid, 6 Amberlyst 7 and triflic acid 8 have been reported to yield myo-inositol 1,3 5-orthoesters in good yields. We have reproduced some of these results in our own lab several times and in all the cases, we got only the corresponding orthoesters but not the 2-O-ester.…”