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Antidiabetes strategies: K. A. Watson, E. P. Mitchell, L. N. Johnson, J. C. Son, C. J. F. Bichard, M. G. Orchard, G. W. J. Fleet, N. G. Oikonomakos, D. D. Leonidas, M. Kontou, A. C. Papageorgiou, Biochemistry 1994, 33, 5745.
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T. D. Butter, R. A. Dwek, F. M. Platt, Chem. Rev. 2000, 100, 4683. For example, N-butyldeoxynojirimycin (NB-DNJ or Zavesca) is a powerful glucosylceramide synthase (GCS) inhibitor and is now approved for use in Europe for the treatment of Gaucher disease, a glycolipid-storage disease.
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26
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28
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a) G. W. J. Fleet, S. K. Namgoong, C. Barker, S. Baines, G. S. Jacob, B. Winchester, Tetrahedron Lett. 1989, 30, 4439;
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c) Y. Blériot, C. R. Veighey, K. H. Smelt, J. Cadefau, W. Stalmans, K. Biggadike, A. L. Lane, M. Müller, D. J. Watkin, G. W. J. Fleet, Tetrahedron: Asymmetry 1996, 7, 2761;
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0034002146
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d) T. D. Butters, L. A. G. M. van den Broek, G. W. J. Fleet, T. M. Krulle, M. R. Wormald, R. A. Dwek, F. M. Platt, Tetrahedron: Asymmetry 2000, 11, 113.
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0033370512
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Asano, N.11
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33
-
-
0041349045
-
-
note
-
Depending on the absolute configuration of adenophorine, either C1 or C5 of structure 3 may be viewed as the pseudoanomeric center.
-
-
-
-
34
-
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0037050415
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B. G. Davis, M. A. T. Maughan, T. M. Chapman, R. Villard, S. Courtney, Org. Lett. 2002, 4, 103.
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35
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0027524581
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B. A. Horenstein, R. F. Zabinski, V. L. Schramm, Tetrahedron Lett. 1993, 34, 7213.
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Horenstein, B.A.1
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36
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0035943311
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a) G. B. Evans, R. H. Furneaux, T. L. Hutchison, H. S. Kezar, P. E. Morris, V. L. Schramm, P. C. Tyler, J. Org. Chem. 2001, 66, 5723;
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Evans, G.B.1
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Tyler, P.C.7
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37
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0034607824
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b) G. B. Evans, R. H. Furneaux, G. J. Gainsford, V. L. Schramm, P. C. Tyler, Tetrahedron 2000, 56, 3053;
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38
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0033490888
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c) R. H. Furneaux, V. L. Schramm, P. C. Tyler, Bioorg. Med. Chem. 1999, 7, 2599;
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Furneaux, R.H.1
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39
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0031584878
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d) R. H. Furneaux, G. Limberg, P. C. Tyler, V. L. Schramm, Tetrahedron 1997, 53, 2915.
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Furneaux, R.H.1
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41
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0013610070
-
-
Additions of carbon nucleophiles to polyhydroxylated imines are rare. See T. Granier, A. Vasella, Helv Chim. Acta 1998, 81, 865 for the addition of trimethylsilyl cyanide.
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Granier, T.1
Vasella, A.2
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42
-
-
0027304330
-
-
By the method of Vasella and co-workers: R. Hoos, A. B. Naughton, A. Vasella, Helv. Chim. Acta 1993, 76, 1802 and by additional methods that will be published elsewhere.
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Helv. Chim. Acta
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Hoos, R.1
Naughton, A.B.2
Vasella, A.3
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43
-
-
0027242167
-
-
By an adaptation of the method of Haines and co-workers: P. A. Fowler, A. H. Haines, R. J. K. Taylor, E. J. T. Chrystal, M. B. Gravestock, Carbohydr. Res. 1993, 246, 377 and by additional methods that will be published elsewhere.
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Fowler, P.A.1
Haines, A.H.2
Taylor, R.J.K.3
Chrystal, E.J.T.4
Gravestock, M.B.5
-
44
-
-
0042350853
-
-
note
-
The signals of 10 may broaden more readily because of smaller differences, relative to those of 9, in the chemical shifts of the two N-epimers in the slow-exchange limit, in addition to, or possibly instead of, differences in inversion exchange rates. Unfortunately, it was not possible to decoalesce the resonances of 10 and thus establish these shift differences.
-
-
-
-
45
-
-
0039570080
-
-
This Saytzev-sense elimination to form a more substituted imine is presumably favored by a high degree of double-bond character in the typically late transition states in imine-forming eliminations. For the formation of Saytzev products in base-catalyzed eliminations in six-membered-ring systems see: N. O. Brace, J. Am. Chem. Soc. 1964, 86, 2428 and M. Bartok, K. Felfoldi, G. Bozoki-Bartok, Helv. Chim. Acta 1980, 63, 2173-2178.
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J. Am. Chem. Soc.
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-
-
Brace, N.O.1
-
46
-
-
0042851830
-
-
This Saytzev-sense elimination to form a more substituted imine is presumably favored by a high degree of double-bond character in the typically late transition states in imine-forming eliminations. For the formation of Saytzev products in base-catalyzed eliminations in six-membered-ring systems see: N. O. Brace, J. Am. Chem. Soc. 1964, 86, 2428 and M. Bartok, K. Felfoldi, G. Bozoki-Bartok, Helv. Chim. Acta 1980, 63, 2173-2178.
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-
-
Bartok, M.1
Felfoldi, K.2
Bozoki-Bartok, G.3
-
47
-
-
0042350850
-
-
For a primary example of the propensity of DBU to yield Saytzev elimination products see H. Oediger, F. Möller, Angew. Chem. 1967, 79, 53; Angew. Chem. Int. Ed. Engl. 1967, 6, 76.
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Angew. Chem.
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-
-
Oediger, H.1
Möller, F.2
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48
-
-
0042851834
-
-
For a primary example of the propensity of DBU to yield Saytzev elimination products see H. Oediger, F. Möller, Angew. Chem. 1967, 79, 53; Angew. Chem. Int. Ed. Engl. 1967, 6, 76.
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-
-
-
49
-
-
0001799213
-
-
-1 (based on the difference in ground-state energy for β-glucopyranose see P. L. Durette, D. Horton, Adv. Carbohydr. Chem. Biochem. 1971, 26, 49), this conformer would be present at <0.001%.
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(1971)
Adv. Carbohydr. Chem. Biochem.
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-
-
Durette, P.L.1
Horton, D.2
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50
-
-
0039570080
-
-
-1 to N-inversion exists at 248 K. Further investigations will be published in due course.
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(1964)
J. Am. Chem. Soc.
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-
-
Bruce, N.O.1
-
56
-
-
0042350849
-
-
note
-
See Supporting Information for a more detailed discussion. Details of further investigations will be published in due course.
-
-
-
-
58
-
-
0000016992
-
-
a) R. B. Woodward, F. E. Bader, H. Bickel, A. J. Frey, R. W. Kierstad, Tetrahedron 1958, 1;
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Tetrahedron
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Woodward, R.B.1
Bader, F.E.2
Bickel, H.3
Frey, A.J.4
Kierstad, R.W.5
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61
-
-
0041349040
-
-
note
-
[9c] Further details will be published in due course.
-
-
-
|