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(D/L)-1,2;4,5-Di-O-cyclohexylidene-myo-inositol was synthesized according to literature methods: Dreef, C. E.; Tulnman, R. J.; Lefeber, A. W. M. Tetrahedron 1991, 47, 4709. The assignment of the diastereomers was made by comparison with the product of phosphorylation of a sample of the resolved diol of known absolute configuration: Vacca, J. P.; deSolms, S. J.; Huff, J. R.; Billington, D. C.; Baker, R.; Kulagowski, J. J.; Maver, I. M. Tetrahedron 1989, 45, 5679; 1991, 47, 907 (corrigenda).
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(D/L)-1,2;4,5-Di-O-cyclohexylidene-myo-inositol was synthesized according to literature methods: Dreef, C. E.; Tulnman, R. J.; Lefeber, A. W. M. Tetrahedron 1991, 47, 4709. The assignment of the diastereomers was made by comparison with the product of phosphorylation of a sample of the resolved diol of known absolute configuration: Vacca, J. P.; deSolms, S. J.; Huff, J. R.; Billington, D. C.; Baker, R.; Kulagowski, J. J.; Maver, I. M. Tetrahedron 1989, 45, 5679; 1991, 47, 907 (corrigenda).
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corrigenda
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(D/L)-1,2;4,5-Di-O-cyclohexylidene-myo-inositol was synthesized according to literature methods: Dreef, C. E.; Tulnman, R. J.; Lefeber, A. W. M. Tetrahedron 1991, 47, 4709. The assignment of the diastereomers was made by comparison with the product of phosphorylation of a sample of the resolved diol of known absolute configuration: Vacca, J. P.; deSolms, S. J.; Huff, J. R.; Billington, D. C.; Baker, R.; Kulagowski, J. J.; Maver, I. M. Tetrahedron 1989, 45, 5679; 1991, 47, 907 (corrigenda).
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0345392944
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note
-
16O. Using these values, the predicted ratio for the resonances from the trans ester (A:B:C) for inversion of configuration is 40.6:34.9:24.5, whereas for retention of configuration the ratios would be 40.6:24.5:34.9. The experimental ratios A:B:C of 40.5:33.5: 26 are in excellent agreement with complete inversion of configuration (the ratios for the cis esters are, of course, complementary).
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28
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0022432723
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