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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 24, 1994 - Issue 6
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Original Articles

A Simple Synthesis of D-Myo-Inositol 4-Phosphate and D-Myo-Inositol 6-Phosphate

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Pages 809-817 | Received 13 Sep 1993, Published online: 16 Feb 2007

References

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  • Bruzik , K. S. , Myers , J. and Tsai , M.-D. 1992 . Tetrahedron Lett. , 33 : 1009
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  • 1989 . Eur. J. Biochem. , 180 : 485 By this system all myo-inositol derivatives are named and numbered as D-myo-inositols regardless of whether the substituents occupy the lowest numbered positions in the resulting name. For example, the enantiomer of D-myo-inositol 1-phosphate is D-myo-inositol 3-phosphate (not L-myo-inositol 1-phosphate)In this communication we are using the stereospecific numbering system for myo-inositol described by the International Union of Biochemistry:
  • Vacca , J. P. , de Solms , S. J. , Huff , J. R. , Billington , D. C. , Baker , R. , Kulagowski , J. J. and Mawer , I. M. 1989 . Tetrahedron , 45 : 5679 Compound 1 and its enantiomer have been prepared enantioselectively previously:
  • 1991 . Tetrahedron , 47 : 907 corrected optical rotation measurements were reported later
  • Garegg , P. J. , Iversen , T. , Johansson , R. and Lindberg , B. 1984 . Carbohydr Res. , 130 : 322
  • Jiang , C. and Baker , D. C. 1986 . J. Carbohydr Chem. , 5 : 615 We substituted comercially available (American Tokyo Kasei, Inc., Portland OR.) 1,1-dimethoxycyclohexane for 1-ethoxycyclohexene in the synthesis of 2. See also:
  • Yu , K.-L. and Fraser-Reid , B. 1988 . Tetrahedron Lett. , 29 : 979
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  • The dimer shown, 5, incorporates two molecules of inositol diol 2 with the same absolute configuration. It is also possible that the dimer formed in the the presence of the racemic 2 incorporates two diols of opposite absolute configuration. This possibility does not affect the rationalization suggested to account for the observed regiochemistry of acylation and alkylation
  • Vacca , J. P. , de Solms , S. J. and Huff , J. R. 1987 . J. Am. Chem. Soc. , 109 : 3478
  • Clark , T. M. and Switzer , R. L. 1977 . Experimental Biochemistry, , 2ed. , 161 – 2 . San Francisco : Freeman W. H. .

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