1,4-anti induction in C-glycosylation of pentose glycals

Tetrahedron Letters

Volumn 39, Issue 14, 1998, Pages 1917-1920

  Hosokawa, Seijiro ^a   Kirschbaum, Bettina ^a   Isobe, Minoru ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PENTOSE;

ARTICLE; CARBOHYDRATE METABOLISM; CONFORMATIONAL TRANSITION; GLYCOSYLATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0032473853     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00047-1     Document Type: Article

References (18)

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11. (c) Babirad, S. A.; Wang, Y.; Kishi, Y. J. Org. Chem., 1987, 52, 1370-1372. See review: M. H. D. Postema, C-Glycoside Synthesis, CRC Press (1995). D. E. Levy, C. Tang, The Chemistry Of C-Glycosides, Pergamon (1995). S. Hanessian, Total Synthesis of Natural Products: The Chiron Approach, Pergamon Press (1983).
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13. (c) Babirad, S. A.; Wang, Y.; Kishi, Y. J. Org. Chem., 1987, 52, 1370-1372. See review: M. H. D. Postema, C-Glycoside Synthesis, CRC Press (1995). D. E. Levy, C. Tang, The Chemistry Of C-Glycosides, Pergamon (1995). S. Hanessian, Total Synthesis of Natural Products: The Chiron Approach, Pergamon Press (1983).
14. 4. R. L. Whistler, et al. Methods in Carbohydrate Chemistry 1962, vol. 1, pp. 84, 184. M. W. Bredenkamp, C. W. Holzapfel, F. Toerien, Synthetic Commun. 1992, 22, 2459.
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16. 5. The oxygen nucleophile (2-propanol) gave 21 even in low selectivity as syn:anti = 25 : 75, which might be produced under equilibrium conditions. (Formula presented)
17. 6. Performed with MacroModel Version 6.0 employing MMFF94 force field as a package program. Merck Molecular Force Field, I. Basis from Scope Parametarization and performance of "MMFF94. Halgren, T. A. J. Comput. Chem. 1996, 17, 490-512.
18. 7. The authors are grateful to Prof. Deslongchamps to notify about their manuscript: Miljkovic, M.; Yeagley, D.; Deslongchamps, P.; Dory, Y. J. Org. Chem., in press.