Synthesis of 6a-Carba-α- and 6a-Carba-β-D-fructopyranose from an enzymatically resolved cyclohexanetriol building block

Synlett

Volumn , Issue 7, 2000, Pages 971-974

  Hubrecht, Idzi ^a   Van Der Eycken, Erik ^b   Van Der Eycken, Johan ^a  

^a GHENT UNIVERSITY   (Belgium)

^b UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

Carba sugars; Carbocycles; Carbohydrates; Pseudo sugars; Stereoselective synthesis

Indexed keywords

PYRANOSIDE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; SYNTHESIS;

EID: 0033929915     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (30)

1. (a) Suami, T. Top. Curr. Chem. 1990, 154, 257-283;
2. (b) Suami, T., Ogawa, S. Adv. Carbohydr. Chem. Biochem. 1990, 48, 21-90.
3. (a) Greco, M. N.; Maryanoff, B. E. Tetrahedron Lett. 1992, 33, 5009-5012;
4. (b) Maryanoff, B. E.; Costanzo, M. J.; Shank, R. P.; Schupsky, J. J.; Ortegon, M. E.; Vaught, J. L. Bioorg. Med. Chem. Lett. 1993, 3, 2653-2656;
5. (c) Maryanoff, B. E.; Costanzo, M. J.; Nortey, S. O.; Greco, M. N.; Shank, R. P.; Schupsky, J. J.; Ortegon, M. P.; Vaught, J. L. J. Med. Chem. 1998, 41, 1315-1343;
6. (c) Costanzo, M. J.; Maryanoff, B. E.; McComsey, D. F.; Nortey, S. O. U.S. Patent 5498629, 1996.
7. Ogawa, S.; Uematsu, Y.; Yoshida, S.; Sasaki, N.; Suami, T. J. Carbohydr. Chem. 1987, 6, 471-478.
8. (a) Shing, T. K. M.; Tang, Y. J. Chem. Soc., Chem. Commun. 1990, 748-749;
9. (b) Shing, T. K. M.; Tang, Y. Tetrahedron 1991, 47, 4571-4578;
10. (c) McComsey, D. F.; Maryanoff, B. E. J. Org. Chem. 1994, 59, 2652-2654.
11. Dumortier, L.; Van der Eycken, J.; Vandewalle, M. Tetrahedron Lett. 1989, 30, 3201-3204.
12. Dumortier, L., Liu, P., Dobbelaere, S.; Van der Eycken, J., Vandewalle, M. Synlett 1992, 243-245.
13. Dumortier, L., Van der Eycken, J., Vandewalle, M. Synlett 1992, 245-246.
14. Takano, S.; Tomita, S.; Iwabuchi, Y.; Ogasawara, K. Synthesis 1988, 610-611.
15. Hodges, P. J.; Procter, G. Tetrahedron Lett. 1985, 26, 4111-4114.
16. Alcaraz, L.; Harnett, J. J.; Miokowski, C.; Martel, J. P.; Le Gall, T.; Dong-Soo Shin; Falck, J. R. Tetrahedron Lett. 1994, 35, 5449-5452.
17. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467.
18. Payne, G. B. J. Org. Chem. 1962, 59, 3819-3822.
19. Spectroscopic properties and optical rotation of product 2 were identical in all respects with those reported.5
20. 2), 69.4 (CH), 73.7 (CH), 75.1 (CH), 75.4 (C); MS (70 eV): m/e (relative intensity): 147 (18) (M-31), 129 (28), 111 (66), 83 (65), 73 (100).
21. 2), 71.0 (CH), 72.4 (CH), 74.1 (CH), 75.6 (C); MS (70 eV): m/e (relative intensity): 147 (58) (M - 31), 129 (42), 111 (100), 83 (73), 73 (44).
22. 3), 74.7 (CH), 77.8 (CH), 84.5 (CH), 109.0 (C).
23. 3), 51.9 (CH), 52.2 (CH), 70.6 (CH), 70.7 (CH), 108.8 (C).
24. 2), 108.7 (C), 145.8 (C).
25. 2), 59.0 (C), 70.8 (CH), 73.7 (CH), 80.3 (CH), 108.8(C).
26. 2J = 15.0 Hz), 2.58 (1H, d, J = 5.0 Hz), 3.08 (1H, dd, J = 1.1 Hz [W-coupling], 5.0 Hz), 3.94 (1H, dd, J = 5.1 Hz, 7.5 Hz), 3.98 (1H, bd, J = 7.5 Hz), 4.36 (1H, m). (figure presented)
27. 2), 74.2 (CH), 75.1 (C), 75.6 (CH), 81.6 (CH), 109.4(C).
28. 3).
29. 2J = 11.8 Hz), 3.66 (1H, d, J = 7.9 Hz), 3.92 (1H, dd, J = 5.4 Hz, 7.9 Hz), 4.28 (1H, m).
30. 2), 73.0 (CH), 75.0 (CH), 79.8 (CH), 83.5 (C), 108.4 (C), 109.0 (C).