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For recent reviews of nucleoside chemistry and modified nucleosides in oligonucleotide synthesis, see: (a) Huryn, D. M.; Okabe, M. Chem. Rev. 1992, 92, 1745-1768.
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(b) Lin, Y.; Qiu, Q.; Gill, S. C.; Jayasena, S. D. Nucleic Acid Res. 1994, 22, 5229-5234.
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(a) Glinski, R. P.; Khan, M. S.; Kalamas, R. L.; Sporn, M. B. J. Org. Chem. 1973, 38, 4299-4305.
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Glinski, R.P.1
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(a) Kirshenheuter, G.; Zhai, Y.; Pieken, W. A. Tetrahedron Lett. 1994, 35, 8517-8520.
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0043058567
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reference 3
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(c) reference 3
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(d) Xi, Z.; Agback, P.; Plavec, J.; Sandström, A.; Chattopadhyaya, J. Tetrahedron 1992, 48, 349-370.
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Xi, Z.1
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0000040986
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(a) Codington, J. F.; Fecher, R.; Fox, J. J. J. Org. Chem. 1962, 27, 163-167.
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0002062166
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R.T. Walker; De Clercq, E.; Eckstein, F., Eds.; Plenum Press: New York, and references therein
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(b) Moffatt, J.G. in Nucleoside Analogues; R.T. Walker; De Clercq, E.; Eckstein, F., Eds.; Plenum Press: New York, 1979; 71-164 and references therein.
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Moffatt, J.G.1
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16
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0001297631
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For recent examples and references, see: (a) Knapp, S.; Kukkola, P. J.; Sharma, S.; Pietranico, S. Tetrahedron Lett. 1987, 28, 5399-5402.
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Sharma, S.3
Pietranico, S.4
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21
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84986671052
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(a) In a recent paper, Mikhailopulo et al suggested an intramolecular anhydronucleoside ring opening reaction to account for an unexpected minor product, see: Mikhailopulo, I. A.; Zaitseva, G. V.; Vaaks, E. V.; Balzarini, J.; De Clercq, E.; Rosemeyer, H.; Seela, F. Liebigs Ann. Chem. 1993, 513-519.
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Mikhailopulo, I.A.1
Zaitseva, G.V.2
Vaaks, E.V.3
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De Clercq, E.5
Rosemeyer, H.6
Seela, F.7
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22
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0043058554
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(b) Intramolecular ring opening of a 2,2′-anhydrouridine by a phosphate has been reported, see: Ogilvie, K. K.; Iwacha, D. Can. J. Chem. 1970, 48, 862-864.
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Ogilvie, K.K.1
Iwacha, D.2
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23
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0042557581
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note
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2,2′-Anhydrouridine is prepared from uridine and diphenyl carbonate (DMF/ HMPA; 110°C) on a kilogram scale according to the published procedure.6
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24
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0041555556
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note
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13C NMR spectra, and C, H, N analysis or mass spectra.
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25
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0000762868
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For an example of intramolecular cyclofunctionalization of an epoxy alcohol-derived trichloroacetimidate, see: Bernet, B.; Vasella, A. Tetrahedron Lett. 1983, 24, 5491-5494.
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Tetrahedron Lett.
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Bernet, B.1
Vasella, A.2
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27
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0042056693
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note
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During the DBU catalyzed cyclization of OTBDMS derivative 12, a minor amount (9% isolated yield) of a cyclization product resulting from nucleophilic attack by the carbamate carbonyl oxygen was formed, as was a significant amount of N-O desilylated product (36%).
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28
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9644285669
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(a) Sonogashira, K.; Tohda, Y., Hagihara, N. Tetrahedron Lett. 1975, 16, 4467-4470.
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Tetrahedron Lett.
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Sonogashira, K.1
Tohda, Y.2
Hagihara, N.3
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31
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0029161984
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(b) Dewey, T. M.; Mundt, A.A.; Crouch, G. J.; Zyzniewski. M. C.; Eaton, B. E. J. Amer. Chem. Soc. 1995, 117, 8474-8475.
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Dewey, T.M.1
Mundt, A.A.2
Crouch, G.J.3
Zyzniewski, M.C.4
Eaton, B.E.5
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32
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0041555549
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note
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5-Iodouridine is unstable under these reaction conditions.
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