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Practical synthesis of enantiomerically pure myo-inositol derivatives

✍ Scribed by Karol S. Bruzik; Jeffrey Myers; Ming-Daw Tsai

Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
246 KB
Volume
33
Category
Article
ISSN
0040-4039

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✦ Synopsis

The synthesis of enontiomericully pure mycQnosiio/ derivatives is accomplished using a mandeiic acid&rived acy/ protecting group. A number of synthetic schemes leading to enantiomerieally pure, and properly functionalized derivatives of myo-inositol start from one of the three positional isomers of di-O-cyclohexylidene-myoinositol.lv2 These derivatives are formed as a mixture, and thus have to be separated by a combination of crystallization and chromatographic techniques,2 making their availability difficult. In contrast, cis-monoacetals of myo-inositol are synthesized in one step in good yield.3 Recently we have found that cis-monoacetals can be selectively protected at the l-hydroxyl group with bulky acylating or silylating reagents.4 By applying selective protection of the remaining hydroxyl groups a number of useful intermediates for the synthesis of phosphoinositides can be obtained, In this communication we report on the synthesis of novel synthetic precursors of inositol-1,4,5_trisphosphate (IP31, phosphatidylinositol

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