Synthesis of 6-deoxy-L-idose and L-acovenose from 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Carbohydrate Research

Volumn 331, Issue 4, 2001, Pages 369-374

  Hung, Shang Cheng ^a   Thopate, Shankar R ^a   Puranik, Ramachandra ^a  

^a INSTITUTE OF CHEMISTRY   (Taiwan)

Author keywords

6 Deoxy L idose; 6 Deoxy L talose; L Acovenose

Indexed keywords

HYDROGENATION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

REGIOSELECTIVE PROTECTION;

CARBOHYDRATES;

1,2:5,6 DI O ISOPROPYLIDENE ALPHA DEXTRO GLUCOFURANOSE; 6 DEOXY LEVO IDOSE; CARBOHYDRATE DERIVATIVE; LEVO ACOVENOSE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHEMICAL STRUCTURE; HYDROGENATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

DEOXY SUGARS; GLUCOSE; HEXOSES; STEREOISOMERISM;

EID: 0035938006     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(01)00058-1     Document Type: Article

References (30)

1. Collins P.M. Dictionary of Carbohydrates. 1998;Chapman and Hall, London.
2. Uchio Y., Nagasaki M., Eguchi S., Matsuo A., Nakayama M., Hayashi S. Tetrahedron Lett. 21:1980;3775-3778.
3. Synthesis of 6-deoxy-L-ido sugars: (a) Hung, S. -C.; Puranik, R.; Chi, F. -C. Tetrahedron Lett. 2000, 41, 77-80.
4. (b) Hiebl, J.; Zbiral, E. Monatsh. Chem. 1990, 121 691-695.
5. (c) Ikeda, D.; Tsuchiya, T.; Umezawa, S. Bull. Chem. Soc. Jpn. 1971, 44, 2529-2537.
6. (d) Wolfrom, M. L.; Hanessian, S. J. Org. Chem. 1962, 27, 1800-1804.
7. (e) Goto, H.; Mori, M.; Tejima, S. Chem. Pharm. Bull. 1978, 26, 1926-1929.
8. (f) Thiem, J.; Kluge, H. -W.; Schwentner, J. Chem. Ber. 1980, 113, 3497-3504.
9. (g) Chiba, T.; Sinaÿ, P. Carbohydr. Res. 1986, 151, 379-389.
10. Synthesis of 6-deoxy-L-talo sugars: (a) Banaszek, A. J. Carbohydr. Chem. 1994, 13, 285-291.
11. (b) Kerékgyártó, J.; Szurmai, Z.; Lipták, A. Carbohydr. Res. 1993, 245, 65-80.
12. (c) Mukaiyama, T.; Shina, I.; Kobayashi, S. Chem. Lett. 1990, 2201-2204.
13. (d) Mori, M.; Tejima, S.; Niwa, T. Chem. Pharm. Bull. 1986, 34, 4037-4044.
14. (e) Defaye, J.; Gadelle, A. Carbohydr. Res. 1984, 126, 165-169.
15. (f) Nelson, V.; El Khadem, H. S. J. Med. Chem. 1983, 26, 1527-1530.
16. (g) Aspinall, G. O.; Takeo, K. Carbohydr. Res. 1983, 121, 61-77.
17. (h) El Khadem, H. S.; Nelson, V. Carbohydr. Res. 1981, 98, 195-201.
18. (i) Garegg, P. J.; Samuelsson, B. Carbohydr. Res. 1978, 67, 267-270.
19. (j) Collins, P. M.; Overend, W. G. J. Chem. Soc. 1965, 1912-1918.
20. Fukuhara K.-I., Murao S., Nozawa T., Hatano M. Tetrahedron Lett. 23:1982;2319-2322.
21. Aspinall G.O., Khare N.K., Sood R.K., Chatterjee D., Rivoire B., Brennan P.J. Carbohydr. Res. 216:1991;357-373.
22. Perry M.B., Maclean L.M., Brisson J.-R., Wilson M.E. Eur. J. Biochem. 242:1996;682-688.
23. Jann B., Shashkov A., Torgov V., Kochanowski H., Seltmann G., Jann K. Carbohydr. Res. 278:1995;155-165.
24. Euw J.V., Reichstein T. Helv. Chim. Acta. 33:1950;485-502.
25. Pathirana C., Tapiolas D., Jensen P.R., Dwight R., Fenical W. Tetrahedron Lett. 32:1991;2323-2326.
26. Synthesis of L-acovenose: (a) Lipták, A.; Kerékgyártó, J.; Popsavin, V.; Kajtár-Peredy, M.; Radics, L. J. Carbohydr. Chem. 1988, 7, 337-357.
27. (b) Kapur, B. M.; Allgeier, H. Helv. Chim. Acta 1968, 51, 89-94.
28. Hodosi G., Podányi B., Kuszmann J. Carbohydr. Res. 230:1992;327-342.
29. Pangborn A.B., Giardello A., Grubbs R.H., Rosen R.K., Timmers F.J. Organometallics. 15:1996;1518-1520.
30. Still W.C., Kahn M., Mitra A. J. Org. Chem. 43:1978;2923-2925.