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Syntheses of Optically Active 2,3,6-Tri-O-benzyl-D-myo-inositol, Laminitol, and Mytilitol from D-Glucose

Ken-ichi Sato, Masayuki Bokura, Makoto Taniguchi
1994 Bulletin of the Chemical Society of Japan  
2,3,6-Tri-O-benzyl-D-myo-inositol, which is a key intermediate of D-inositol 1,4,5-triphosphate, was synthesized from D-glucose without performing any optical resolution by utilizing C2 symmetry. Laminitol and mytilitol were also synthesized from D-glucose via the same key intermediate, 1D-{1,3/2,4)-tetra-O-benzyl-2-Cmethyl-5-cyclohexene-1,2,3,4-tetrol. Since the discovery of the role of o-myo-inositol 1,4, 5-triphosphate (IP3, 1) as an intracellular second messenger for calcium mobilization,l)
more » ... ium mobilization,l) the biological interest in IP 3 has greatly increased. In order to explore the biochemical process, a simple, general, and efficient methodology for the chemical syntheses of 1 and its derivatives is required that will act as agonists in the phosphoinositide system. 2) The biological importance of other stereoisomers of inositol is less well established. 3 ) However, there are two known naturally-occurring Cmethyl inositols, both isolated from algae: (-)-laminitol (3) and mytilitol (4) (Chart 1). Compound 3 is especially interesting in that it has the myo-inositoltype configuration with a methyl group at C-4, and that it inhibits the growth of Neurospora crassa. 4 ) Syntheses of racemic laminitol from myo-inositol 5 ) and (-)laminitol from toluene 6l have been reported. To date, however, for the syntheses of 1 and its derivatives, naturally occurring cyclitol derivatives, myo-inositol,7) quebrachitol,8) and quinic acid 9 ) have been mainly used as the starting materials. In general, optical resolution has been required in the case of using myo-inositol, which has a plane of symmetry. We now report on novel synthetic methods of optically active laminitol and mytilitol, as well as details concerning a
doi:10.1246/bcsj.67.1633 fatcat:5hl6ht5x6be45ghyv5rttcptla