Synthesis of 1- and 3-C-(aminomethyl)-1,2,3,4,5-cyclohexanepentols from (+)-epi-quercitol

Journal of Carbohydrate Chemistry

Volumn 20, Issue 7-8, 2001, Pages 703-717

  Ogawa, Seiichiro ^a   Aoyama, Hiroshi ^a   Tezuka, Yoji ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035527801     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1081/CAR-100108284     Document Type: Article

References (16)

1. th anniversary.
2. 6 and Other Rice Components, Kyoto, June 8-9, 1999, Abstract PS-64; Takahashi, A.; Kanbe, K.; Tamamura, T.; Sato, K. Bioconversion of myo-inositol to Rare Cyclic Sugar Alcohols. Anticancer Res. 1999, 3807.
3. 6 and Other Rice Components, Kyoto, June 8-9, 1999, Abstract PS-64; Takahashi, A.; Kanbe, K.; Tamamura, T.; Sato, K. Bioconversion of myo-inositol to Rare Cyclic Sugar Alcohols. Anticancer Res. 1999, 3807.
4. Ogawa, S.; Uetsuki, Y.; Tezuka, Y. Synthesis and Evaluation of Glucocerebrosidase Inhibitory Activity of Anhydro Deoxyinositols from (+)-epi-and (-)-vibo-Quercitols. Bioorg. Med. Chem. Lett. 1999, 9, 1493-1498.
5. Kameda, Y.; Asano, N.; Yoshikawa, M.; Takeuchi, M.; Yamaguchi, T.; Matsui, K.; Hori, S.; Fukase, H. Valiolamine, a New α-Glucosidase Inhibiting Aminocyclitol Produced by Streptomyces hygroscopicus. J. Antibiot. 1984, 37, 1301-1307; Kameda, Y.; Asano, N.; Takeuchi, M.; Yamaguchi, T.; Matsui, K.; Horii, S.; Fukase, H. Epivaliolamine and Deoxyvalidamine, New Pseudo-Aminosugars Produced by Streptomyces hygroscopicus. ibid. 1985, 38, 1816-1818; Kameda, Y.; Asano, N.; Yamaguchi, K.; Matsui, S.; Horii, S.; Fukase, H. Validamycin G and Validoxylamine G, New Members of the Validamycins. ibid. 1986, 39, 1491-1494.
6. Kameda, Y.; Asano, N.; Yoshikawa, M.; Takeuchi, M.; Yamaguchi, T.; Matsui, K.; Hori, S.; Fukase, H. Valiolamine, a New α-Glucosidase Inhibiting Aminocyclitol Produced by Streptomyces hygroscopicus. J. Antibiot. 1984, 37, 1301-1307; Kameda, Y.; Asano, N.; Takeuchi, M.; Yamaguchi, T.; Matsui, K.; Horii, S.; Fukase, H. Epivaliolamine and Deoxyvalidamine, New Pseudo-Aminosugars Produced by Streptomyces hygroscopicus. ibid. 1985, 38, 1816-1818; Kameda, Y.; Asano, N.; Yamaguchi, K.; Matsui, S.; Horii, S.; Fukase, H. Validamycin G and Validoxylamine G, New Members of the Validamycins. ibid. 1986, 39, 1491-1494.
7. Kameda, Y.; Asano, N.; Yoshikawa, M.; Takeuchi, M.; Yamaguchi, T.; Matsui, K.; Hori, S.; Fukase, H. Valiolamine, a New α-Glucosidase Inhibiting Aminocyclitol Produced by Streptomyces hygroscopicus. J. Antibiot. 1984, 37, 1301-1307; Kameda, Y.; Asano, N.; Takeuchi, M.; Yamaguchi, T.; Matsui, K.; Horii, S.; Fukase, H. Epivaliolamine and Deoxyvalidamine, New Pseudo-Aminosugars Produced by Streptomyces hygroscopicus. ibid. 1985, 38, 1816-1818; Kameda, Y.; Asano, N.; Yamaguchi, K.; Matsui, S.; Horii, S.; Fukase, H. Validamycin G and Validoxylamine G, New Members of the Validamycins. ibid. 1986, 39, 1491-1494.
8. Ogawa, S.; Uchida, C.; Ohhira, T. Synthesis of Two New Stereoisomers of Valiolamine through Ring Expansion of 5-Amino-2,3,4-trihydroxycyclopentane-1-one derivatives with Diazomethane. Carbohydr. Lett. 1999, 3, 277-284.
9. 1,6eq = 3.6 Hz), respectively.
10. A complex mixture of products was formed when catalysts other than Raney nickel were used.
11. The reaction conditions have not fully optimized to furnish the spiro epoxides selectively.
12. 4
13. Uchida, C.; Kimura, H.; Ogawa, S. Synthesis and Biological Evaluation of Potent Glycosidse Inhibitors: TV-Phenyl Cyclic Isourea Derivatives of 5-Amino-and 5-Amino-C-(hydroxymethyl)-1,2,3,4-cyclopentanetetraols. Bioor. Med. Chem. 1997, 5, 921-939.
14. Biological assay toward sucrase and maltase was carried out by Dr. A. Takahashi.
15. Very recently, 5a-carba-L-fucopyranose derivatives, having a branched-aminomethyl function at C-1, have been demonstrated to possess a strong inhibitory activity against α-L-fucosidase (bovine kidney): Ogawa, S.; Maruyama, A.; Odagiri, T.; Yuasa, H.; Hashimoto, H. Synthesis and Biological Evaluation of α-L-Fucosidase Inhibitors: 5a-Carba-α-L-fucopyranosylamine and Related Compounds. Eur. J. Org. Chem. 2001, 967-974.
16. 2O).