A highly stereoselective synthesis of α-Linked C-glycopyranosides using 2,2'-azobis-(2,4-dimethyl-4-methoxyvaleronitrile) (V-70)

Tetrahedron Letters

Volumn 38, Issue 48, 1997, Pages 8345-8348

  Kita, Yasuyuki ^a   Gotanda, Kentoku ^a   Sano, Atsunori ^b   Oka, Masahisa ^b   Murata, Kenji ^a   Suemura, Miki ^a   Matsugi, Masato ^a  

^a OSAKA UNIVERSITY   (Japan)

^b FUJIFILM Wako Pure Chemical Corporation   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2,2' AZOBIS(2,4 DIMETHYL 4 METHOXYVALERONITRILE); ENZYME INHIBITOR; GLYCOPYRANOSIDE; RADICAL; TETRYLAMMONIUM BROMIDE; UNCLASSIFIED DRUG;

ARTICLE; BINDING KINETICS; CARBOHYDRATE ANALYSIS; ENZYME INHIBITION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; TEMPERATURE MEASUREMENT;

EID: 0030695204     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10259-3     Document Type: Article

References (21)

1. (a) Connor, D. T.; Greenough, R. C. and von Strandtmann, M. J. J. Org. Chem. 1977, 42, 3664-3669;
2. (b) Moore, R. E. and Bartoline, G. J. J. Am. Chem. Soc. 1981, 103, 2491-2494;
3. (c) Shulmann, M. L.; Shilyan, S. D. and Khorlin, A. Y. Carbohydr. Res. 1974, 33, 229-235;
4. (d) Chmielewski, M.; BeMiller, J. N. and Cerretti, D. P. ibid. 1981, 97, C1-C4.
5. (a) Kozikowski, A. P. and Sorgi, K. L. Tetrahedron Lett. 1982, 23, 2281-2284;
6. (b) Lewis, M. D.; Cha, J. K. and Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976-4978;
7. (c) Reed, L. A.; Ito, Y.; Masamune, S. and Sharpless, K. B. ibid, 1982, 104, 6468-6470;
8. (d) Schmidt, R. R. and Hoffmann, M. Angew. Chem. Int. Ed. Engl. 1983, 22, 406.
9. A review see: Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599.
10. (a) Giese, B.; Dupuis, J. and Nix, M. Org. Synth. 1987, 65, 236-239;
11. (b) Giese, B. and Dupuis, J. Angew. Chem. Int. Ed. Engl. 1983, 22, 622-623.
12. (a) Robertson, J. A. U. S. Patent 2,586,995 (1952) [Chem. Abstr. 1952, 46, 9579c].
13. (b) Lim, D. Collect. Czechoslov. Chem. Commun. 1968, 33, 1122-1130.
14. (c) Shinohara, N.; Kudo, M.; Iwabuchi, M. Jpn. Kokai Tokkyo Koho JP 04,66,588 [92,66,588] (Cl. C07F7/12), 02 Mar 1992, Appl. 90/172,449, 29 Jun 1990; 4pp. [Chem. Abstr. 1992, 117,26799b]
15. (d) Satsuka, H.; Takasu, Y. Jpn. Kokai Tokkyo Koho JP 06,172,232 [94,172,232] (Cl. C07C22/04), 21 Jun 1994, Appl. 92/329,416, 09 Dec 1992; 6pp. [Chem. Abstr. 1994, 121, 230457a]
16. (e) Katsura, T.; Shiratani, H. Eur. Pat. Appl. EP 709,369 (Cl. C07C253/30),1 May 1996, JP Appl. 94/289,079, 27 Oct 1994; 7pp. [Chem. Abstr. 1996, 125, 58121f]. 2,2′-Azobis-(2,4-dimethyl-4-methoxyvaleronitrile) is commercially available from Wako Pure Chemical Ind., Ltd., (Japan), and V-70 is its trade name. This compound is a mixture of diastereomeric isomers whose melting points are 58 °C and 107 °C and should be stored below -10 °C to prevent any decomposition. V-70 is stable in a refrigerator for a few months, and the pure V-70 can be easily obtained by the following procedure: V-70 (10.0 g, ca. 90% content) was added to dry acetone (20ml) at -10 °C with stirring. The heterogeneous solution was stirred for 30 min at -10 °C. Collecting the crystalline precipitates afforded 6.2g of pure V-70 (62%, >99% content).
17. Kita, Y.; Sano, A.; Yamaguchi, T.; Oka, M.; Gotanda, K. and Matsugi, M. Tetrahedron Lett. 1997, 38, 3549-3552.
18. Giese, B. and Witzel, T. Angew. Chem. Int. Ed. Engl. 1986, 25, 450-451.
19. For an example: "Anomeric Effect: Origin and Consequences"; Szarek, W. A.; Horton, D.; Eds.; American Chemical Society: Washington, D. C., 1979; ACS Symp. Ser. No. 87.
20. (a) Collins, P. M.; Premartne, P.; Manro, A. and Hussain, A. Tetrahedron Lett. 1989, 30, 4721-4722;
21. (b) Lemieux, R. U.; Hendriks, K. B.; Stick, R. V. and James, K. J. Am. Chem. Soc. 1975, 97, 4056-4062.