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1
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0000759694
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1. Reviews: Davis, A. P. Chem. Soc. Rev. 1993, 22, 243; Davis, A. P.; Bonar-Law, R. P.; Sanders, J. K. M. in Comprehensive Supramolecular Chemistry; Murakami, Y., Ed.; Pergamon: Oxford, 1996; Vol. 4, p 257; Walliman, P.; Marti, T.; Furer, A.; Diederich, F. Chem. Rev, 1997, 97, 1567; Li, Y. X.; Dias, J. R. Chem. Rev. 1997, 97, 283.
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Davis, A.P.1
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2
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0000759694
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Murakami, Y., Ed.; Pergamon: Oxford
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1. Reviews: Davis, A. P. Chem. Soc. Rev. 1993, 22, 243; Davis, A. P.; Bonar-Law, R. P.; Sanders, J. K. M. in Comprehensive Supramolecular Chemistry; Murakami, Y., Ed.; Pergamon: Oxford, 1996; Vol. 4, p 257; Walliman, P.; Marti, T.; Furer, A.; Diederich, F. Chem. Rev, 1997, 97, 1567; Li, Y. X.; Dias, J. R. Chem. Rev. 1997, 97, 283.
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Comprehensive Supramolecular Chemistry
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Davis, A.P.1
Bonar-Law, R.P.2
Sanders, J.K.M.3
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3
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0001593086
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1. Reviews: Davis, A. P. Chem. Soc. Rev. 1993, 22, 243; Davis, A. P.; Bonar-Law, R. P.; Sanders, J. K. M. in Comprehensive Supramolecular Chemistry; Murakami, Y., Ed.; Pergamon: Oxford, 1996; Vol. 4, p 257; Walliman, P.; Marti, T.; Furer, A.; Diederich, F. Chem. Rev, 1997, 97, 1567; Li, Y. X.; Dias, J. R. Chem. Rev. 1997, 97, 283.
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Chem. Rev.
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Walliman, P.1
Marti, T.2
Furer, A.3
Diederich, F.4
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4
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0000097162
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1. Reviews: Davis, A. P. Chem. Soc. Rev. 1993, 22, 243; Davis, A. P.; Bonar-Law, R. P.; Sanders, J. K. M. in Comprehensive Supramolecular Chemistry; Murakami, Y., Ed.; Pergamon: Oxford, 1996; Vol. 4, p 257; Walliman, P.; Marti, T.; Furer, A.; Diederich, F. Chem. Rev, 1997, 97, 1567; Li, Y. X.; Dias, J. R. Chem. Rev. 1997, 97, 283.
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Chem. Rev.
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Li, Y.X.1
Dias, J.R.2
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5
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0028100318
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Examples of special relevance: (a) Boyce, R.; Li, G.; Nestler, H. P.; Suenaga, T.; Still, W. C. J. Am. Chem. Soc. 1994, 116, 7955.
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J. Am. Chem. Soc.
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Boyce, R.1
Li, G.2
Nestler, H.P.3
Suenaga, T.4
Still, W.C.5
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6
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0029925955
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(b) Cheng, Y. A.; Suenaga, T.; Still, W. C. J. Am. Chem. Soc. 1996, 118, 1813.
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J. Am. Chem. Soc.
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Cheng, Y.A.1
Suenaga, T.2
Still, W.C.3
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7
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0028590192
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(c) Hsieh, H.-P.; Muller, J. G.; Burrows, C. J. J. Am. Chem. Soc. 1994, 116, 12077.
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Hsieh, H.-P.1
Muller, J.G.2
Burrows, C.J.3
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8
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0030906528
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Ref. 1d contains a preliminary mention of N-protected 2, as a starting material for a potent electroneutral anionophore
-
(d) Davis, A. P.; Perry, J. J.; Williams, R. P. J. Am. Chem. Soc. 1997, 119, 1793. Ref. 1d contains a preliminary mention of N-protected 2, as a starting material for a potent electroneutral anionophore.
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J. Am. Chem. Soc.
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Davis, A.P.1
Perry, J.J.2
Williams, R.P.3
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9
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0001025460
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2. (a) Cheng, Y.; Ho, D. M.; Gottlieb, C. R.; Kahne, D.; Bruck, M. A. J. Am. Chem. Soc. 1992, 114, 7319;
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Cheng, Y.1
Ho, D.M.2
Gottlieb, C.R.3
Kahne, D.4
Bruck, M.A.5
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10
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0000676012
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(b) Venkatasan, P.; Cheng, Y.; Kahne, D. J. Am. Chem. Soc. 1994, 116, 6955;
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Venkatasan, P.1
Cheng, Y.2
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11
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0031040423
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(c) Janout, V.; Lanier, M.; Regen, S. L. J. Am. Chem. Soc. 1997, 119, 640.
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Janout, V.1
Lanier, M.2
Regen, S.L.3
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12
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0001291104
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For a general leading refernce to facial amphiphiles, see: (d) McQuade, D. T.; Barrett, D. G.; Desper, J. M.; Hayashi, R. K.; Gellman, S. H. J. Am. Chem. Soc. 1995, 117, 4862.
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McQuade, D.T.1
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Desper, J.M.3
Hayashi, R.K.4
Gellman, S.H.5
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13
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0030445091
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-
3. See refs. 1a,b and: (a) Wess, G.; Bock, K.; Kleine, H.; Kurz, M.; Guba, W.; Hemmerle, H.; LopezCalle, E.; Baringhaus, K. H.; Glombik, H.; Enhsen, A.; Kramer, W. Angew. Chem., Int. Ed. Engl. 1996, 35, 2222;
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Angew. Chem., Int. Ed. Engl.
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Wess, G.1
Bock, K.2
Kleine, H.3
Kurz, M.4
Guba, W.5
Hemmerle, H.6
LopezCalle, E.7
Baringhaus, K.H.8
Glombik, H.9
Enhsen, A.10
Kramer, W.11
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14
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21844516666
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(b) Kasal, A.; Kohout, L.; Lebl, M. Coll. Czech. Chem. Comm. 1995, 60, 2147.
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Coll. Czech. Chem. Comm.
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Kasal, A.1
Kohout, L.2
Lebl, M.3
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15
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0010519947
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-
note
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4. Cf. the secondary hydroxyl groups in 1 which are not, by themselves, sufficiently hydrophilic to promote solubility in water. See discussion later in the text.
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-
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16
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0025778312
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5. Batta, A. K.; Aggarwal, S. K.; Salen, G.; Schefer, S. J. Lipid Res. 1991, 32, 977.
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J. Lipid Res.
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Batta, A.K.1
Aggarwal, S.K.2
Salen, G.3
Schefer, S.4
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17
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84985507208
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6. Giordano, C.; Perdoncin, G.; Castaldi, G. Angew. Chem., Int. Ed. Engl. 1985, 24, 499.
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(1985)
Angew. Chem., Int. Ed. Engl.
, vol.24
, pp. 499
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Giordano, C.1
Perdoncin, G.2
Castaldi, G.3
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18
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0010520871
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-
note
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7. While both 3α and 7β positions are equatorial, it seems that the former is slightly more exposed. A small amount of diol formed by over-reaction could be bis-acetylated for recycling.
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-
-
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19
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0026045538
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8. For previous work on the reduction of steroidal oximes, see refs. 1c, 3b and: Schneider, S.; Schramm, U.; Schreyer, A.; Buscher, H.-P.; Gerok, W.; Kurz, G. J. Lipid Res. 1991, 32, 1755; Ahmed, S.; Alauddin, M.; Caddy, B.; Smith, M. M.; Sidwell, W. T. L. Aust. J. Chem. 1971, 24, 521; Sato, Y. Bull. Chem. Soc. Japan 1965, 38, 1581; Guthrie, J. P. Can. J. Chem. 1972, 50, 3993.
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J. Lipid Res.
, vol.32
, pp. 1755
-
-
Schneider, S.1
Schramm, U.2
Schreyer, A.3
Buscher, H.-P.4
Gerok, W.5
Kurz, G.6
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20
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-
84971020080
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-
8. For previous work on the reduction of steroidal oximes, see refs. 1c, 3b and: Schneider, S.; Schramm, U.; Schreyer, A.; Buscher, H.-P.; Gerok, W.; Kurz, G. J. Lipid Res. 1991, 32, 1755; Ahmed, S.; Alauddin, M.; Caddy, B.; Smith, M. M.; Sidwell, W. T. L. Aust. J. Chem. 1971, 24, 521; Sato, Y. Bull. Chem. Soc. Japan 1965, 38, 1581; Guthrie, J. P. Can. J. Chem. 1972, 50, 3993.
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(1971)
Aust. J. Chem.
, vol.24
, pp. 521
-
-
Ahmed, S.1
Alauddin, M.2
Caddy, B.3
Smith, M.M.4
Sidwell, W.T.L.5
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21
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-
0013805653
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-
8. For previous work on the reduction of steroidal oximes, see refs. 1c, 3b and: Schneider, S.; Schramm, U.; Schreyer, A.; Buscher, H.-P.; Gerok, W.; Kurz, G. J. Lipid Res. 1991, 32, 1755; Ahmed, S.; Alauddin, M.; Caddy, B.; Smith, M. M.; Sidwell, W. T. L. Aust. J. Chem. 1971, 24, 521; Sato, Y. Bull. Chem. Soc. Japan 1965, 38, 1581; Guthrie, J. P. Can. J. Chem. 1972, 50, 3993.
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(1965)
Bull. Chem. Soc. Japan
, vol.38
, pp. 1581
-
-
Sato, Y.1
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22
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0000181014
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8. For previous work on the reduction of steroidal oximes, see refs. 1c, 3b and: Schneider, S.; Schramm, U.; Schreyer, A.; Buscher, H.-P.; Gerok, W.; Kurz, G. J. Lipid Res. 1991, 32, 1755; Ahmed, S.; Alauddin, M.; Caddy, B.; Smith, M. M.; Sidwell, W. T. L. Aust. J. Chem. 1971, 24, 521; Sato, Y. Bull. Chem. Soc. Japan 1965, 38, 1581; Guthrie, J. P. Can. J. Chem. 1972, 50, 3993.
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(1972)
Can. J. Chem.
, vol.50
, pp. 3993
-
-
Guthrie, J.P.1
-
23
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0026767678
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-
9. For related conversions, see: Davis, A. P.; Orchard, M. G. Tetrahedron Lett. 1992, 33, 5111; Davis, A. P.; Dresen, S.; Lawless, L. J. Tetrahedron Lett. 1997, 38, 4305.
-
(1992)
Tetrahedron Lett.
, vol.33
, pp. 5111
-
-
Davis, A.P.1
Orchard, M.G.2
-
24
-
-
0030919027
-
-
9. For related conversions, see: Davis, A. P.; Orchard, M. G. Tetrahedron Lett. 1992, 33, 5111; Davis, A. P.; Dresen, S.; Lawless, L. J. Tetrahedron Lett. 1997, 38, 4305.
-
(1997)
Tetrahedron Lett.
, vol.38
, pp. 4305
-
-
Davis, A.P.1
Dresen, S.2
Lawless, L.J.3
-
25
-
-
0010493397
-
-
note
-
8 requires C, 67.09; H, 9.75; N, 5.72%.
-
-
-
-
27
-
-
0010519948
-
-
note
-
+ at pH ~ 7.5-10. Precipitation was apparent at pH >9.5.
-
-
-
-
29
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-
0028097350
-
-
14. Cf. the antibacterial effects of squalamine, and other amino-steroids: Moriarty, R. M.; Tuladhar, S. M.; Guo, L.; Wehrli, S. Tetrahedron Lett. 1994, 35, 8103; Sadownik, A.; Deng, G.; Janout, V.; Regen, S. L. J. Am. Chem. Soc. 1995, 117, 6138.
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(1994)
Tetrahedron Lett.
, vol.35
, pp. 8103
-
-
Moriarty, R.M.1
Tuladhar, S.M.2
Guo, L.3
Wehrli, S.4
-
30
-
-
0001366519
-
-
14. Cf. the antibacterial effects of squalamine, and other amino-steroids: Moriarty, R. M.; Tuladhar, S. M.; Guo, L.; Wehrli, S. Tetrahedron Lett. 1994, 35, 8103; Sadownik, A.; Deng, G.; Janout, V.; Regen, S. L. J. Am. Chem. Soc. 1995, 117, 6138.
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(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 6138
-
-
Sadownik, A.1
Deng, G.2
Janout, V.3
Regen, S.L.4
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