-
1
-
-
0033524870
-
-
For the initial publication in the series, see: Tang, X.-Q.; Liao, X.-M.; Piccirilli, J. A. J. Org. Chem. 1999, 64, 747.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 747
-
-
Tang, X.-Q.1
Liao, X.-M.2
Piccirilli, J.A.3
-
2
-
-
0029036849
-
-
and references therein
-
(a) Yoshimura, Y.; Satoh, H.; Sakata, S.; Ashida, N.; Miyazaki, S.; Matsuda, A. Nucleosides Nucleotides 1995, 14, 427 and references therein.
-
(1995)
Nucleosides Nucleotides
, vol.14
, pp. 427
-
-
Yoshimura, Y.1
Satoh, H.2
Sakata, S.3
Ashida, N.4
Miyazaki, S.5
Matsuda, A.6
-
3
-
-
0028178019
-
-
(b) Cory, A. H.; Samano, V.; Robins, M. J.; Cory, J. P. Biochem. Pharmacol. 1994, 47, 365.
-
(1994)
Biochem. Pharmacol.
, vol.47
, pp. 365
-
-
Cory, A.H.1
Samano, V.2
Robins, M.J.3
Cory, J.P.4
-
4
-
-
0028223989
-
-
Awano, H.; Shuto, S.; Baba, M.; Kira, T.; Shigeta, S.; Matsuda, A. Bioorg. Med. Chem. Lett. 1994, 4, 367.
-
(1994)
Bioorg. Med. Chem. Lett.
, vol.4
, pp. 367
-
-
Awano, H.1
Shuto, S.2
Baba, M.3
Kira, T.4
Shigeta, S.5
Matsuda, A.6
-
5
-
-
0025737572
-
-
(a) Baker, C. H.; Banzon, J.; Bollinger, J. M.; Stubbe, J.; Samano, V.; Robin, M. J.; Lippert, B.; Jarvi, E.; Resvick, R. J. Med. Chem. 1991, 34, 1879.
-
(1991)
J. Med. Chem.
, vol.34
, pp. 1879
-
-
Baker, C.H.1
Banzon, J.2
Bollinger, J.M.3
Stubbe, J.4
Samano, V.5
Robin, M.J.6
Lippert, B.7
Jarvi, E.8
Resvick, R.9
-
6
-
-
0027385019
-
-
(b) Ong, S. P.; McFarlan, S. C.; Hogenkamp, H. P. C. Biochemistry 1993, 32, 11397.
-
(1993)
Biochemistry
, vol.32
, pp. 11397
-
-
Ong, S.P.1
McFarlan, S.C.2
Hogenkamp, H.P.C.3
-
7
-
-
0030036601
-
-
(c) van der Donk, W. A.; Yu, G.; Silva, D. J.; Stubbe, J.; McCarthy, J. R.; Jarvi, E. T.; Matthews, D. P.; Resvick, R. J.; Wagner, E. Biochemistry 1996, 35, 8381.
-
(1996)
Biochemistry
, vol.35
, pp. 8381
-
-
Van Der Donk, W.A.1
Yu, G.2
Silva, D.J.3
Stubbe, J.4
McCarthy, J.R.5
Jarvi, E.T.6
Matthews, D.P.7
Resvick, R.J.8
Wagner, E.9
-
8
-
-
0038060317
-
-
(a) Walton, E.; Jenkins, S. R.; Nutt, R. F.; Zimmerman, M.; Holly, F. W. J. Am. Chem. Soc. 1966, 88, 4524.
-
(1966)
J. Am. Chem. Soc.
, vol.88
, pp. 4524
-
-
Walton, E.1
Jenkins, S.R.2
Nutt, R.F.3
Zimmerman, M.4
Holly, F.W.5
-
9
-
-
0014489225
-
-
(b) Walton, E.; Jenkins, S. R.; Nutt, R. F.; Holly, F. W.; Nemes, M. J. Med. Chem. 1969, 12, 306.
-
(1969)
J. Med. Chem.
, vol.12
, pp. 306
-
-
Walton, E.1
Jenkins, S.R.2
Nutt, R.F.3
Holly, F.W.4
Nemes, M.5
-
13
-
-
0030894115
-
-
Harry-O'kuru, R. E.; Smith, J. M.; Wolfe, M. S. J. Org. Chem. 1997, 62, 1754.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 1754
-
-
Harry-O'kuru, R.E.1
Smith, J.M.2
Wolfe, M.S.3
-
14
-
-
0032511950
-
-
and references therein
-
It has been reported that the reactions at C-1 of carbohydrates via cationic intermediates are much more difficult to achieve when a trifluoromethyl group is attached to C-2. Logothetis, T. A.; Eilitz, U.; Hiller, W.; Burger, K. Tetrahedron 1998, 54, 14023 and references therein.
-
(1998)
Tetrahedron
, vol.54
, pp. 14023
-
-
Logothetis, T.A.1
Eilitz, U.2
Hiller, W.3
Burger, K.4
-
15
-
-
0025649186
-
-
Seebach argued on the basis of van der Waal hemispheres that a trifluoromethyl group is between two and three times larger than a methyl group. See: Seebach, D. Angew Chem., Int. Ed. Engl. 1990, 29, 1320. Other assessments suggest that the steric influence of the trifluoromethyl group is closer to that of an isopropyl group or even a tert-butyl group. See: (a) Smart, B. E.; Middleton, W. J. J. Am. Chem. Soc. 1987, 109, 4982.
-
(1990)
Angew Chem., Int. Ed. Engl.
, vol.29
, pp. 1320
-
-
Seebach, D.1
-
16
-
-
0042791385
-
-
Seebach argued on the basis of van der Waal hemispheres that a trifluoromethyl group is between two and three times larger than a methyl group. See: Seebach, D. Angew Chem., Int. Ed. Engl. 1990, 29, 1320. Other assessments suggest that the steric influence of the trifluoromethyl group is closer to that of an isopropyl group or even a tert-butyl group. See: (a) Smart, B. E.; Middleton, W. J. J. Am. Chem. Soc. 1987, 109, 4982.
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 4982
-
-
Smart, B.E.1
Middleton, W.J.2
-
17
-
-
0042290373
-
-
(b) Mosher, H. S.; Stevenot, J. E.; Kimble, D. O. J. Am. Chem. Soc. 1956, 78, 4374.
-
(1956)
J. Am. Chem. Soc.
, vol.78
, pp. 4374
-
-
Mosher, H.S.1
Stevenot, J.E.2
Kimble, D.O.3
-
18
-
-
0027509451
-
-
(c) Ramachandran, P. V.; Teodorovic, A. V.; Brown, H. C. Tetrahedron 1993, 49, 1725.
-
(1993)
Tetrahedron
, vol.49
, pp. 1725
-
-
Ramachandran, P.V.1
Teodorovic, A.V.2
Brown, H.C.3
-
20
-
-
33845183108
-
-
Prakash, G. K. S.; Krishnamurti, R.; Olah, G. A. J. Am. Chem. Soc. 1989, 111, 393.
-
(1989)
J. Am. Chem. Soc.
, vol.111
, pp. 393
-
-
Prakash, G.K.S.1
Krishnamurti, R.2
Olah, G.A.3
-
21
-
-
0042290371
-
-
note
-
19F spectra are different from those of the corresponding 2′-C-β-trifluoromethyl-β-D-uridine 10 described in this paper.
-
-
-
-
22
-
-
0016351762
-
-
(a) Niedballa, U.; Vorbruggen, H. J. Org. Chem. 1974, 39, 3654, 3664, 3668, 3672.
-
(1974)
J. Org. Chem.
, vol.39
, pp. 3654
-
-
Niedballa, U.1
Vorbruggen, H.2
-
25
-
-
0042290372
-
-
note
-
The anomers were separated with difficulty by silica gel chromatography as described in Supporting Information.
-
-
-
-
29
-
-
84987350937
-
-
(d) Currie, B. L.; Robins, R. K.; Robins, M. J. J. Heterocycl. Chem. 1970, 7, 323.
-
(1970)
J. Heterocycl. Chem.
, vol.7
, pp. 323
-
-
Currie, B.L.1
Robins, R.K.2
Robins, M.J.3
-
30
-
-
0021174699
-
-
(e) Ozaki, S.; Watanabe, Y.; Hoshiko, T.; Fujisawa, H.; Uemura, A.; Ohrai, K. Tetrahedron Lett. 1984, 25, 5061.
-
(1984)
Tetrahedron Lett.
, vol.25
, pp. 5061
-
-
Ozaki, S.1
Watanabe, Y.2
Hoshiko, T.3
Fujisawa, H.4
Uemura, A.5
Ohrai, K.6
-
31
-
-
0002057555
-
-
(f). Kissman, H. M.; Pidacks, C.; Baker, B. R. J. Am. Chem. Soc. 1955, 77, 18.
-
(1955)
J. Am. Chem. Soc.
, vol.77
, pp. 18
-
-
Kissman, H.M.1
Pidacks, C.2
Baker, B.R.3
-
32
-
-
0042791383
-
-
(g) Kessman, H. M.; Child, R. G.; Weiss, M. J. J. Am. Chem. Soc. 1957, 79, 1185.
-
(1957)
J. Am. Chem. Soc.
, vol.79
, pp. 1185
-
-
Kessman, H.M.1
Child, R.G.2
Weiss, M.J.3
-
33
-
-
0000962275
-
-
Koch, A.; Lamberth, C.; Wetterich, F.; Giese, B. J. Org. Chem. 1993, 58, 1083.
-
(1993)
J. Org. Chem.
, vol.58
, pp. 1083
-
-
Koch, A.1
Lamberth, C.2
Wetterich, F.3
Giese, B.4
-
36
-
-
0020440848
-
-
A few papers report the reaction of 3,5-di-O-acyl-D-1-ribofuranosyl chloride with reactive pyridine derivatives but not with nucleobases. See: (a) Konno, K.; Hayano, K.; Shirahama, H.; Saito, H.; Matsumoto, T. Tetrahedron 1982, 38, 3281.
-
(1982)
Tetrahedron
, vol.38
, pp. 3281
-
-
Konno, K.1
Hayano, K.2
Shirahama, H.3
Saito, H.4
Matsumoto, T.5
-
37
-
-
0042290368
-
-
(b). Freyne, E. J.; Esmans, E. L.; Lepoivre, J. A.; Alderweireldt, F. C. Carbohydr. Res. 1980, 78, 235.
-
(1980)
Carbohydr. Res.
, vol.78
, pp. 235
-
-
Freyne, E.J.1
Esmans, E.L.2
Lepoivre, J.A.3
Alderweireldt, F.C.4
-
38
-
-
0041288653
-
-
(c) Alderweireldt, F. C.; Kemps, L.; Esmans, E. L.; Dommisse, R. A.; Lepoivre, J. A. Heterocycles 1984, 21, 795.
-
(1984)
Heterocycles
, vol.21
, pp. 795
-
-
Alderweireldt, F.C.1
Kemps, L.2
Esmans, E.L.3
Dommisse, R.A.4
Lepoivre, J.A.5
-
39
-
-
0014816941
-
-
Miles, D. W.; Inskeep, W. H.; Robins, M. J.; Winkley, M. W.; Robins, R. K.; Eyring, H. J. Am. Chem. Soc. 1970, 92, 3872.
-
(1970)
J. Am. Chem. Soc.
, vol.92
, pp. 3872
-
-
Miles, D.W.1
Inskeep, W.H.2
Robins, M.J.3
Winkley, M.W.4
Robins, R.K.5
Eyring, H.6
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