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Examples of compounds proposed to alkylate and/or cleave DNA through quinone methide intermediates include: (a) Zheng, Q.; Rokita, S. E. J. Org. Chem. 1996, 61, 9080-9081.
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For an example of a p-quinone methide forming analogue of CC-1065 with potential DNA alkylating abilities, see: Boger, D. L.; Nishi, T.; Teegarden, B. R. J. Org. Chem. 1994, 59, 4943-4949.
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An elegant aziridinium derivative has been reported to selectively alkylate the DNA phosphodiester backbone: (a) Skibo, E. B.; Schulz, W. G. J. Med. Chem. 1993, 36, 3050-3055.
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A few synthetic methods have been developed to convert dialkyl phosphate salts into trialkyl phosphates: (a) Ayukawa, H.; Ohuch, S.; Ishikawa, M.; Hata, T. Chem. Lett. 1995, 81.
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0345483057
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note
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Complete characterization of a related trapped product will be reported in due course.
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41
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0003601534
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Merck &CO: Whitehouse Station, NJ
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The Merck Index; Budavari, S., Ed.; Merck &CO: Whitehouse Station, NJ, 1996.
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The Merck Index
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Budavari, S.1
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42
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0002947088
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a of the dibenzylphosphoric acid was estimated to be 0.71 in water/chloroform mixture: Courtemanche, P.; Merlin, J.-C. Bull. Soc. Chim. Fr. 1967, 10, 3911-3919.
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Courtemanche, P.1
Merlin, J.-C.2
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43
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0344189183
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note
-
The chemical shifts of the benzylic protons of 2 were 4.85 ppm without MsOH, 4.89 ppm with 0.5 equiv of MsOH, 4.93 ppm with 0.8 equiv of MsOH, and 4.96 ppm with 1.0 equiv of MsOH.
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