On the stereochemistry of aryl C-glycosides: Unusual behavior of bis-TBDPS protected aryl C-olivosides

Tetrahedron Letters

Volumn 37, Issue 5, 1996, Pages 663-666

  Hosoya, Takamitsu ^a   Ohashi, Yoriko ^a   Matsumoto, Takashi ^a   Suzuki, Keisuke ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE;

ARTICLE; DRUG STRUCTURE; STEREOCHEMISTRY;

EID: 0030052926     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02227-9     Document Type: Article

References (18)

1. For reviews on aryl C-glycosides, see: (a) Hacksell, U.; Daves, G. D., Jr. Prog. Med. Chem. 1985, 22, 1.
2. (b) Suzuki, K.; Matsumoto, T. In Recent Progress in the Chemical Synthesis of Antibiotics and Related MicrobialProducts; Lukacs, G., Ed.; Springer: Berlin, 1993; Vol. 2, p 353.
3. For example, see: (a) Matsumoto, T.; Katsuki, M.; Jona, H.; Suzuki, K. J. Am. Chem. Soc. 1991, 113, 6982.
4. (b) Matsumoto, T.; Sohma, T.; Yamaguchi, H.; Kurata, S.; Suzuki, K. Tetrahedron 1995, 51, 7347, and the references cited therein. Note that our C-glycoside samples always have a hydroxyl group to the aryl C-glycoside linkage, as they were prepared via the O→C-glycoside rearrangement (ref 3).
5. For the O→C-glycoside rearrangement, see: Matsumoto, T.; Katsuki, M.; Suzuki, K. Tetrahedron Lett. 1988, 29, 6935. Suzuki, K. Pure Appl. Chem. 1994, 66, 2175.
6. For the O→C-glycoside rearrangement, see: Matsumoto, T.; Katsuki, M.; Suzuki, K. Tetrahedron Lett. 1988, 29, 6935. Suzuki, K. Pure Appl. Chem. 1994, 66, 2175.
7. 7 in which two siloxy substituents are disposed to pseudo-axial orientation, and the ring is of a considerably flat half-chair conformation. (equation presented)
8. Bolitt, V.; Mioskowski, C.; Lee, S.-G.; Falck, J. R. J. Org. Chem. 1990, 55, 5812.
9. 13C-NMR, IR, HRMS and/or combustion analysis.
10. The X-ray crystallographic analyses were kindly performed by Drs. T. Tsuji and K. Ishikawa, Ajinomoto Co., to whom we express deep appreciation.
11. 1H NMR spectra of 3 and 4 supports the analysis.
12. 2ax,3 = 2.4-2.9 Hz.
13. To examine the behavior of β-4, we attempted to prepare it by bis-silylation of the diol, derived from β-5, which failed under a variety of conditions.
14. (a) Eliel, E. L.; Satici, H. J. Org. Chem. 1994, 59, 688.
15. (b) Saito, S.; Hirohara, Y.; Narahara, O.; Moriwake, T. J. Am. Chem. Soc. 1989, 111, 4533.
16. For general discussion on the configuration and conformation of cyclic compounds, see: Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: N.Y., 1994; Chapt. 11.4.
17. One of the referees suggested that we examine the behavior of the corresponding triisopropylsilyl derivative, as the silyl group is known as another extremely large group. The result turned out to be essentially the same as in the TBDPS case described herein. We thank the referee for the suggestion.
18. For an alternative approach to such structures, see: Matsumoto, T.; Sohma, T.; Yamaguchi, H.; Suzuki, K. Chem. Lett. 1995, 677.