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Caine D. Tetrahedron. 57:2001;2643-2684.
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24
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0011101889
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Compound 3 is unstable although it can be stored in the refrigerator without decomposition for 1 week.
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Compound 3 is unstable although it can be stored in the refrigerator without decomposition for 1 week.
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25
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0011112768
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13C NMR spectra.
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13C NMR spectra.
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29
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0011107874
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The derivatives 6 and 7 were analyzed as O,O-diacetates.
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The derivatives 6 and 7 were analyzed as O,O-diacetates.
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32
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0011101890
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The preparation of 8 appeared to be more difficult than we expected, since the bromo derivative 3 readily underwent elimination to give methyl (E)-3-(5-nitro-1,5-dioxaspiro[5.5]undec-5-yl)propenoate, e.g. treatment of 3 with sodium acetate in DMSO at room temperature afforded the O-acetyl derivative of 8 and the unsaturated nitroester in the ratio 1:1. The use of potassium trifluoroacetate decreased the amount of the elimination product to ca. 20%.
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The preparation of 8 appeared to be more difficult than we expected, since the bromo derivative 3 readily underwent elimination to give methyl (E)-3-(5-nitro-1,5-dioxaspiro[5.5]undec-5-yl)propenoate, e.g. treatment of 3 with sodium acetate in DMSO at room temperature afforded the O-acetyl derivative of 8 and the unsaturated nitroester in the ratio 1:1. The use of potassium trifluoroacetate decreased the amount of the elimination product to ca. 20%.
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34
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36
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0011104111
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We tried to obtain derivatives 10a and 13 by reaction of the O-mesyl derivative of 9 with thymine and adenine under basic conditions in DMF, but these attempts failed; 10a was obtained in 5% yield and 13 was not isolated at all.
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We tried to obtain derivatives 10a and 13 by reaction of the O-mesyl derivative of 9 with thymine and adenine under basic conditions in DMF, but these attempts failed; 10a was obtained in 5% yield and 13 was not isolated at all.
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38
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0026554003
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Fairbanks I.A., Carpenter N.C., Fleet G.W.J., Ramsden G.N., de Bello C.I., Winchester B.G., Al-Dahr S.S., Nagahashi G. Tetrahedron. 48:1992;3365-3376.
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Ramsden, G.N.4
De Bello, C.I.5
Winchester, B.G.6
Al-Dahr, S.S.7
Nagahashi, G.8
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0001262709
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Couturier M., Tuckert J.L., Andersen B.M., Dubé P., Negrí J.T. Org. Lett. 3:2001;465-467.
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Couturier, M.1
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Negrí, J.T.5
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40
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0011103209
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Pyrrolidinol 9 was characterized as its O,N-diacetate.
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Pyrrolidinol 9 was characterized as its O,N-diacetate.
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41
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0037182218
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3-benzoyl derivatives of the pyrimidine bases give the same nucleosides in only 30% yield. See: Richichi B., Cicchi S., Chiacchio U., Romeo G., Brandi A. Tetrahedron Lett. 43:2002;4013-4015.
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Richichi, B.1
Cicchi, S.2
Chiacchio, U.3
Romeo, G.4
Brandi, A.5
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