Synthesis of alkyl glycosides using trialkyl borates

Heterocycles

Volumn 53, Issue 6, 2000, Pages 1263-1267

  Yamanoi, Takashi ^a   Iwai, Yoshihiro ^a   Inazu, Toshiyuki ^a  

^a NOGUCHI INSTITUTE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GLYCOSIDE DERIVATIVE; BORINIC ACID DERIVATIVE; GLYCOSIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; JAPAN; MOLECULAR INTERACTION; SYNTHESIS;

EID: 0034211026     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-00-8899     Document Type: Article

References (11)

1. S. Hanessian and A. G. Pernet, Adv. Carbohydr. Chem. Biochem., 1976, 33, 111.
2. K. Toshima and K. Tatsuta, Chem. Rev., 1993, 93, 1503; other references cited therein.
3. J. Inanaga, Y. Yokoyama, and T. Hanamoto, Tetrahedron Lett., 1993, 34, 2791.
4. T. Yamanoi, Y. Iwai, and T. Inazu, J. Carbohydr. Chem., 1998, 17, 819.
5. 3 is also commercially available from Gelest, Inc. (Azuma Co., Ltd.) and Sigma-Aldrich Japan Co., Ltd.
6. The following paper also suggested an enhancement in the reactivity of the alcohol by the formation of a boron-alkoxide: K. Toshima, H. Nagai, Y. Ushiki, and S. Matsumura, Synlett, 1998, 1007.
7. A. J. Ratcliffe and B. Fraser-Reid, J. Chem. Soc., Perkin Trans. I, 1990, 747.
8. The references for the syntheses of the allyl glycoside were cited in the following paper: H. B. Mereyala and S. R. Gurrala, Carbohydr. Res., 1998, 307, 351.
9. T. Takano, F. Nakatsubo, and K. Murakami, Carbohydr. Res., 1990, 203, 341.
10. M.-Z. Liu, H.-N. Fan, Z.-W. Guo, and Y.-Z. Hui, Carbohydr. Res., 1996, 290, 233.
11. 4, the solvent was evaporated under reduced pressure. The crude product was purified by a preparative silica gel TLC (ethyl acetate/hexane) to give the corresponding alkyl glycosides.