Synthesis of 1-C-alkyl-α-d-glucopyranosides by Lewis acid- or Brønsted acid-catalyzed O-glycosidation

Tetrahedron

Volumn 62, Issue 44, 2006, Pages 10383-10392

  Yamanoi, Takashi ^a   Oda, Yoshiki ^a   Matsuda, Sho ^a,b   Yamazaki, Ippo ^a   Matsumura, Kazuhide ^a   Katsuraya, Kaname ^c   Watanabe, Mikio ^b   Inazu, Toshiyuki ^d  

^a NOGUCHI INSTITUTE   (Japan)

^b TOKAI UNIVERSITY   (Japan)

^c WAYO WOMEN'S UNIVERSITY   (Japan)

^d School of Engineering   (Japan)

Author keywords

1 C Alkyl glycopyranose; Br nsted acid; Glycosidation; Ketopyranoside; Lewis acid

Indexed keywords

2,3,4,6 TETRA O BENZYL 1 C METHYL ALPHA DEXTRO GLUCOPYRANOSYL DIMETHYLPHOSPHINOTHIOATE; 2,3,4,6 TETRA O BENZYL ALPHA DEXTRO GLUCOPYRANOSYL 2,3,4,6 TETRA O BENZYL 1 C METHYL ALPHA DEXTRO GLUCOPYRANOSIDE; ACETIC ACID DERIVATIVE; ALKYL GROUP; BENZYL DERIVATIVE; BRONSTED ACID; CARBOHYDRATE DERIVATIVE; CHEMICAL AGENT; CHLORINE DERIVATIVE; GLUCOPYRANOSIDE; LEWIS ACID; METHYL 6 O (1 C BENZYL 2,3,4,6 TETRA O BENZYL ALPHA DEXTRO GLUCOPYRANOSYL) 2,3,4 TRI O BENZYL ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL GROUP; PHENETHYL 1 C BENZYL 2,3,4,6 TETRA O BENZYL ALPHA DEXTRO GLUCOPYRANOSIDE; PHENETHYL 2,3,4,6 TETRA O BENZYL 1 C BUTYL ALPHA DEXTRO GLUCOPYRANOSIDE; PHENETHYL 2,3,4,6 TETRA O BENZYL 1 C ETHYL ALPHA DEXTRO GLUCOPYRANOSIDE; PHENETHYL 2,3,4,6 TETRA O BENZYL 1 C METHYL ALPHA DEXTRO GLUCOPYRANOSIDE; REAGENT; SCANDIUM; SULFONIC ACID DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; DRUG SYNTHESIS; GLYCOSIDATION; POLYMERIZATION; PRIORITY JOURNAL; QUANTUM YIELD; STEREOCHEMISTRY;

TETRA;

EID: 33748685228     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.08.059     Document Type: Article

References (32)

1. Brockhaus M., and Lehmann J. Carbohydr. Res. 53 (1977) 21-31
2. Li X.L., Ohtake H., Takahashi H., and Ikegami S. Synlett (2001) 1885-1888
3. For examples of chemical glycosidation, see:
4. Li X.L., Ohtake H., Takahashi H., and Ikegami S. Tetrahedron 57 (2001) 4283-4295
5. Lin H.-C., Yang W.-B., Gu Y.-F., Chen C.-Y., Wu C.-Y., and Lin C.-H. Org. Lett. 5 (2003) 1087-1089
6. Chang C.-F., Yang W.-B., Chang C.-C., and Lin C.-H. Tetrahedron Lett. 43 (2002) 6515-6519
7. Lin H.-C., Du W.-P., Chang C.-C., and Lin C.-H. Tetrahedron Lett. 46 (2005) 5071-5076
8. For enzymatic glycosidation, see:
9. Schlesselmann P., Fritz H., Lehmann J., Uchiyama T., Brewer C.F., and Hehre E.J. Biochemistry 21 (1982) 6606-6614
10. For example, see:
11. Czernecki S., and Ville G. J. Org. Chem. 54 (1989) 610-612
12. Kraus G.A., and Molina M.T. J. Org. Chem. 53 (1988) 752-753
13. Li X.L., Ohtake H., Takahashi H., and Ikegami S. Tetrahedron 57 (2001) 4297-4309
14. As the analogs of the 1-C-alkyl-hexopyranose derivatives, the glycosidation using the 1-C-alkoxyalkyl-hexopyranose derivatives was reported. See:. Heskamp B.M., Veeneman G.H., van der Marel G.A., van Boeckel C.A.A., and van Boom J.H. Tetrahedron 51 (1995) 5657-5670
15. As the 1-C-alkyl-hexofuranose derivative, the glycosidation using 2,3:5,6-di-O-isopropylidene-1-C-methyl-d-mannofuranosyl acetate was reported. See:. Dondoni A., Marra A., Rojo I., and Scherrmann M.-C. Tetrahedron 52 (1996) 3057-3074
16. Inazu T., and Yamanoi T. Chem. Lett. (1989) 69-72
17. Yamanoi T., and Inazu T. Chem. Lett. (1990) 849-852
18. Yamanoi T., Nakamura K., Takeyama H., Yanagihara K., and Inazu T. Chem. Lett. (1993) 343-346
19. Yamanoi T., Nakamura K., Sada S., Goto M., Furusawa Y., Takano M., Fujioka A., Yanagihara K., Satoh Y., Hosokawa H., and Inazu T. Bull. Chem. Soc. Jpn. 66 (1993) 2617-2622
20. Yamanoi T., Nakamura K., Takeyama H., Yanagihara K., and Inazu T. Bull. Chem. Soc. Jpn. 67 (1994) 1359-1366
21. Yamanoi T., Fujioka A., and Inazu T. Bull. Chem. Soc. Jpn. 67 (1994) 1488-1491
22. Yamanoi T., Iwai Y., and Inazu T. J. Carbohydr. Chem. 17 (1998) 819-822
23. Yamanoi T., Iwai Y., and Inazu T. Heterocycles 53 (2000) 1263-1267
24. Yamanoi T., and Yamazaki I. Tetrahedron Lett. 42 (2001) 4009-4011
25. Yamanoi T., Oda Y., Yamazaki I., Shinbara M., Morimoto K., and Matsuda S. Lett. Org. Chem. 2 (2005) 242-246
26. Yamanoi T., Matsuda S., Yamazaki I., Inoue R., Hamasaki K., and Watanabe M. Heterocycles 68 (2006) 673-677
27. We also reported the Brønsted acid-catalyzed intramolecular β-glycosidation of 1-C-alkyl-d-hexopyranoses to form the anhydroketopyranoses;. Yamanoi T., Matsumura K., Matsuda S., and Oda Y. Synlett (2005) 2973-2977
28. Kuzuhara H., and Fletcher Jr. H.G. J. Org. Chem. 32 (1967) 2531-2534
29. Inazu, T.; Yamanoi, T. Jpn. Kokai Tokkyo Koho, JP 02240093, 1990.
30. 2,3,4,6-Tetra-O-benzyl-1-C-methyl-α-d-glucopyranosyl acetate has also been synthesized from 1 by a multistep reaction sequence;. Fukase H., and Horii S. J. Org. Chem. 57 (1992) 3642-3650
31. 2O gave the open ring compound;. Heskamp B.M., Noort D., van der Marel G.A., and van Boom J.H. Synlett (1992) 713-715
32. Inanaga J., Yokoyama Y., and Hanamoto T. Tetrahedron Lett. 34 (1993) 2791-2794