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2142683999
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note
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3 catalyzed C-O coupling reaction of DHA gave only a trace amount (under 10% yield) of the target product, 5D, which was judged by NMR.
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24
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0000117587
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The formation of AHA has been a problem when moderate excess of TMS triflate or TMSCI are used to activate DHA. (a) Bennek, J. A.; Gray, G. R. J. Org. Chem. 1987, 52, 892-897.
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0035804312
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(c) O'Neill, P. M.; Miller, A.; Bishop, L. P. D.; Hindley, S.; Maggs, J. L.; Ward, S. A.; Roberts, S. M.; Scheinmann, F.; Stachulski, A. V.; Posner, G. H.; Park, B. K. J. Med. Chem. 2001, 44, 58-68.
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27
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0001183739
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2-catalyzed C-O coupling reaction. A similar glycosylation of sugar, which was activated by TMS triflate, has been reported. Our proposed mechanism shows that the stability of the ketals (3a and 3c) and TMS ether (TMSOMe and TMSOAc, and TMSOTMS) could be responsible for the difference in the final coupling yields. (a) Tietze, L. F.; Fisher, R; Guder, H. T.; Goerlach, A.; Neumann, M.; Krach, T. Carbohydr. Res. 1987, 164, 177-194.
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28
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0026661315
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(b) Lin, A. J.; Li, L.; Andersen, S. L.; Klayman, D. L. J. Med. Chem. 1992, 35, 1639-1642.
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29
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0346025403
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(c) The coupling of aminosugars catalyzed by TMS triflate was doubly activated by introducing a trichloro-oxazoline group into the substrate. Donohoe, T. J.; Logan, J. G.; Laffan, D. D. P. Org. Lett. 2003, 5, 4995-4998.
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30
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2142741276
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note
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(d) The real catalyst may be triflic acid after TMS triflate is consumed.
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31
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2142735697
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note
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Compound 8 was soluble in neutral (pH = 7.35) phosphate buffer (<3 mg/mL).
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