Synthesis and structure of glycosylidene acetals of galactoside

Heterocycles

Volumn 47, Issue 2, 1998, Pages 685-688

  Ohtake, Hiro ^a   Iimori, Takamasa ^a   Shiro, Moto ^b   Ikegami, Shiro ^a  

^a TEIKYO UNIVERSITY   (Japan)

^b RIGAKU CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001105761     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-97-s(n)106     Document Type: Article

References (16)

1. (a) D. E. Wright, Tetrahedron, 1979, 35, 1207.
2. (b) W. D. Ollis, C. Smith and D. E. Wright, Tetrahedron, 1979, 35, 105.
3. (a) J. Yoshimura and M. Tamaru, Carbohydr. Res., 1979, 72, C9.
4. (b) M. Tamaru, S. Horito and J. Yoshimura, Bull. Chem. Soc. Jpn., 1980, 53, 3687.
5. (c) J. Yoshimura, S. Horito and H. Hashimoto, Chem. Lett., 1981, 375.
6. (d) S. Horito, K. Asano, K. Umemura, H. Hashimoto and J. Yoshimura, Carbohydr. Res., 1983, 121, 175.
7. (e) J. Yoshimura, S. Horito, J. Tamura and H. Hashimoto, Chem. Lett., 1985, 1335.
8. (f) J. Tamura, S. Horito, H. Hashimoto and J. Yoshimura, Carbohydr. Res., 1988, 174, 181.
9. T. Tsunoda, M. Suzuki and R. Noyori, Tetrahedron Lett., 1980, 21, 1357.
10. (a) H. Ohtake, T. Iimori and S. Ikegami, Tetrahedron Lett., 1997, 38, 3413.
11. (b) T. Iimori, H. Ohtake and S. Ikegami, Tetrahedron Lett., 1997, 38, 3415.
12. Kurihara and a co-worker have reported the ketal formation by using diol, sec- or tert-alkoxysilane and TMSOTf; M. Kurihara and N. Miyata, Chem. Lett., 1995, 263.
13. 13C-Chemical shifts of anormeric carbons (C-1′) in interglycosidic orthoesters: see for example; N. Neuss, K. F. Koch, B. B. Molloy, W. Day, L. L. Huckstep, D. E. Dorman and J. D. Roberts, Helv. Chim. Acta, 1970, 53, 2314;
14. A. K. Ganguly, O. Z. Sarre, D. Greeves and J. Morton, J. Am. Chem. Soc., 1975, 97, 1982.
15. The X-Ray analytical data are available on request.
16. Dimethyl or methyl trimethylsilyl acetals of sugar lactones are known to be formed from sugar lactones and TMSOMe in the presence of TMSOTf; J. Yoshimura, S. Horito, K. Asano and H. Hashimoto, Tennen Yuki Kagobutsu Toronkai Koen Yoshishu, 24th (Japan), 1981, p. 638.