Preferred Conformation of C-Glycosides. 3. Preferred Conformation of Carbon Analogues of 1,4-Disaccharides

Journal of Organic Chemistry

Volumn 52, Issue 21, 1987, Pages 4825-4827

  Babirad, Stefan A ^a   Wang, Yuan ^a   Goekiian, Peter G ^a   Kishi, Yoshito ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

C GLYCOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

DRUG STRUCTURE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRELIMINARY COMMUNICATION; THEORETICAL STUDY;

EID: 0023612869     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00230a040     Document Type: Letter

References (6)

1. Wu, T. C. ; Goekjian, P. G.; Kishi, Y. J. Org. Chem. preceding paper in this issue, Goekjian, P. G.; Wu, T. C. ; Kang, H. Y. ; Kishi, Y. J. Org. Chem., second preceding paper in this issue.
2. Babirad, S. A.; Wang, Y.; Kishi, Y. J. Org. Chem. 1987, 52, 1370.
3. The importance of this type of 1,3-diaxial-like interactions for the conformational preference of carbohydrates was first recognized by Horton and co-workers. For example, see: El Khadem, H. S.; Horton, D. J. Org. Chem. 1968, 33, 734.
4. Applying a modified Karplus equation (Haasnoot, C. A. G.; de Leeuw, F. A. A. M.; Aliona, C. Tetrahedron 1980, 36, 2783), the following torsional angles (and ip, respectively) were obtained: 1, 50° and 80°; 2, 50° and 85°; 3, -80° and -90°; 4, -70° and -85°; 5, 40° and 5°; 6, 85° and -5°; 7, -80° and -10°; 8, -90° and -5°. For the definition of and \p, see ref 17e in ref lb.
5. For the conformational analysis of cellobiose and maltose in solution, for example, see: Shashkov, A. S.; Lipkind, G. M.; Kochetkov, N. K. Carbohydr. Res. 1986,147, 175 and references cited therein, Nardin, R.; Saint-Germain, J.; Vincendon, M.; Taravel, F.; Vignon, M. Nouv. J. Chim. 1984, 8, 305 and references cited therein, Lemieux, R. U.; Bock, K.; Delbaere, L. T. J.; Koto, S.; Rao, V. S. Can. J. Chem. 1980, 58, 631 and references cited therein, St. Jacques, M.; Sundararajan, P. R.; Taylor, K. J.; Marchessault, R. H. J. Am. Chem. Soc. 1976, 98, 4386 and references cited therein.
6. (10)There are a number of excellent review articles on this subject. For example, see: Lemieux, R. U. Chem. Soc. Rev. 1978, 7,423. Frontiers of Chemistry, Laidler, K. J. Ed.; Pergamon: New York; 1982; p 1 and references cited therein.