Multigram scale synthesis of formyl tetra-O-benzyl-β-D-C-glucopyranoside using benzothiazole as a formyl group equivalent

Tetrahedron Letters

Volumn 44, Issue 1, 2003, Pages 13-16

  Dondoni, Alessandro ^a   Marra, Alberto ^a  

^a UNIVERSITY OF FERRARA   (Italy)

Author keywords

Benzothiazole; C glycosides; Sugar aldehydes; Thiazole

Indexed keywords

ALDEHYDE; BENZOTHIAZOLE; FORMYL TETRA O BENZYL BETA DEXTRO C GLUCOPYRANOSIDE; GLUCOPYRANOSIDE; KETOSE; LACTONE DERIVATIVE; SODIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COLUMN CHROMATOGRAPHY; CRYSTALLIZATION; DRUG SYNTHESIS; HEATING; LOW TEMPERATURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXYGENATION; PURIFICATION;

EID: 0037212994     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02525-X     Document Type: Article

References (34)

1. Postema M.H.D. Rees C.W. C-Glycoside Synthesis. 1995;CRC Press, Boca Raton, FL.
2. Levy D.E., Tang C. Baldwin J.E., Magnus P.D. The Chemistry of C-Glycosides. 1995;Elsevier Science Ltd, Oxford.
3. Marcaurelle L.A., Bertozzi C.R. Chem. Eur. J. 5:1999;1384.
4. Glaudemans C.P.J. Chem. Rev. 91:1991;25.
5. Wang J., Kovác P., Sinaÿ P., Glaudemans C.P.J. Carbohydr. Res. 308:1998;191.
6. Dondoni A., Boscarato A., Zuurmond H.-M. Tetrahedron Lett. 37:1996;7587.
7. Dondoni A., Zuurmond H.M., Boscarato A. J. Org. Chem. 62:1997;8114.
8. Dondoni A., Kleban M., Zuurmond H., Marra A. Tetrahedron Lett. 39:1998;7991.
9. Dondoni A., Giovannini P.P., Marra A. Tetrahedron Lett. 41:2000;6195.
10. Dondoni A., Mizuno M., Marra A. Tetrahedron Lett. 41:2000;6657.
11. Dondoni A., Formaglio P., Marra A., Massi A. Tetrahedron. 57:2001;7719.
12. Dondoni A., Marra A., Mizuno M., Giovannini P.P. J. Org. Chem. 67:2002;4186.
13. Dondoni A., Giovannini P.P., Perrone D. J. Org. Chem. 67:2002;7203.
14. Dondoni A., Junquera F., Merchán F.L., Merino P., Scherrmann M.-C., Tejero T. J. Org. Chem. 62:1997;5484.
15. Dondoni A., Massi A., Marra A. Tetrahedron Lett. 39:1998;6601.
16. Dondoni A., Marra A., Massi A. J. Org. Chem. 64:1999;933.
17. Dondoni A., Marra A. Tetrahedron Lett. 43:2002;1649.
18. Dondoni A., Scherrmann M.-C. Tetrahedron Lett. 34:1993;7319.
19. Dondoni A., Scherrmann M.-C. J. Org. Chem. 59:1994;6404.
20. For recent reviews, see: (a) Dondoni, A. Synthesis 1998, 1681; (b) Dondoni, A. Pure Appl. Chem. 2000, 72, 1577.
21. For recent reviews, see: (a) Dondoni, A. Synthesis 1998, 1681; (b) Dondoni, A. Pure Appl. Chem. 2000, 72, 1577.
22. 3 in the unmasking protocol gives the α-linked aldehyde 10 in pure form and 85% yield (see the experimental procedure in Ref. 10). In a similar way the β-linked aldehyde 11 is obtained in 86% yield.
23. 3 for 3 days at rt. Afterwards, a partial conversion into 11 was observed.
24. Labéguère F., Lavergne J.-P., Martinez J. Tetrahedron Lett. 43:2002;7271.
25. Lasterra Sánchez M.E., Michelet V., Besnier I., Gênet J.P. Synlett. 1994;705.
26. No reference to this work was given in Ref. 11.
27. Corey E.J., Boger D.L. Tetrahedron Lett. 19:1978;5.
28. Chikashita H., Itoh K. Heterocycles. 23:1985;295.
29. Known lactone 7 (Kuzuhara, H.; Fletcher, H. J. Org. Chem. 1967, 32, 2531) was prepared on a 5-15 g scale in quantitative yield by oxidation of the corresponding hemiacetal with pyridinium chlorochromate (Corey, E. J.; Suggs, J. W. Tetrahedron Lett. 1975, 16, 2647).
30. Known lactone 7 (Kuzuhara, H.; Fletcher, H. J. Org. Chem. 1967, 32, 2531) was prepared on a 5-15 g scale in quantitative yield by oxidation of the corresponding hemiacetal with pyridinium chlorochromate (Corey, E. J.; Suggs, J. W. Tetrahedron Lett. 1975, 16, 2647).
31. 6a,6b=11.4 Hz, H-6a), 3.72 (dd, 1 H, H-6b).
32. 6a,6b=11.6 Hz, H-6a), 3.84-3.80 (m, 2 H, H-5, H-6b), 3.67 (d, 1 H, H-2), 2.24 (s, 3 H, Ac).
33. 5,6=3.2 Hz, 2 H-6), 3.70 (ddd, 1 H, H-5).
34. 5,6=9.7 Hz, H-5), 3.51 (ddd, 1 H, H-6), 3.39 (dd, 1 H, H-2), 3.28 (d, 1 H, OH), 3.26 (d, 1 H, OH).