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0344161321
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note
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We thank Dr. S. L. Beaucage for proposing an epimerization mechanism. (equation presented)
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0345023956
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note
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The synthesis of diol (R)-and (S)-14 was scaled up by Dalton Chemical Laboratories, Inc., Ontario, Canada. The chiral auxiliaries 5c and 5d were synthesized in (S) configuration because of the avaiable of starting material (S)-14.
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0344592917
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note
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Although nitrile 5b (96% ee) was used, only two diastereomers of indolyl-oxazaphosphorine 7b were observed. Probably because of the limitation of detection, the minor compounds could not be detected.
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0344161320
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note
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A mixture of dry dichloromethane and acetonitrile (1:10) was used as eluting solvent. Using ethyl acetate instead of acetonitrile gave very low yield of 7b. The trace of acids in ethyl acetate probably accelerated the decomposition of 7b.
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25
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0345023954
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note
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The snake venom phosphodiesterase and P1 nuclease digestion and HPLC analysis were carried out at ISIS Pharmaceuticals (Carlsbad, CA) by Dr. M. Manoharan.
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Wang, J.-C.; Just, G.; Guzaev, A. P.; Manoharan, M. J. Org. Chem. 1999, 64, 2595.
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Wang, J.-C.1
Just, G.2
Guzaev, A.P.3
Manoharan, M.4
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