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Chiral synthesis of D-myo-inositol 1-phosphate starting from L-quebrachitol

✍ Scribed by Takahiko Akiyama; Naoto Takechi; Shoichiro Ozaki

Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
149 KB
Volume
31
Category
Article
ISSN
0040-4039

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✦ Synopsis

D-M~ -inositol l-phosphate was synthesized from L-quebrachitol via stereoselective inversion of a 3-hydroxyl group and chemoselective demethylation.

Recently, inositol phosphates have stimulated considerable attention from the standpoint of its biosynthesis, function, and metabolism since the discovery that D-myo-inositol 1,4,5&phosphate (Ins( 1,4,5)P3) acts as the probable intracelluar second messenger for calcium mobilization. 1 A number of synthetic procedures for inositol phosphates have appeared so far. 2 A drawback of these syntheses is that tedious optical resolution is necessary in synthesizing chiral mositol phosphates. To develop a practical synthesis of biologically active Dmyo -inositol phosphates, we focused on L-quebrachitol (~-2-o -methyl-cGo -inositol),3 obtained from an

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## Abstract Synthesis of __LL, DD__ and __LD__ stereoisomers of di‐__myo__‐inositol‐1,1′‐phosphate (DIP) could be realised by phosphitylation of properly protected __L__‐ or __D__‐__myo__‐inositol derivatives. It was also established that naturally occurring (+)‐DIP has the __LL__‐configuration.

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t\_-Quebrachitol was O-demethylated to give lt\_-chiro-inositol which, on treatment with dibutyltin oxide, benzyl chloride, and tetrabutylammonium iodide in acetonitrile, gave mainly crystalline lo-2,3,5tri-0-benzyl-chiro-inositol (Sal together with lt\_-2,3,5,6-tetra-0-benzyl-chiro-inositol. Catal