Synthesis of fused pyran-carbahexopyranoses as glycosidase inhibitors

Carbohydrate Research

Volumn 344, Issue 5, 2009, Pages 606-612

  Doddi, Venkata Ramana ^a   Kancharla, Pavan K ^a   Reddy, Y Suman ^a   Kumar, Amit ^a   Vankar, Yashwant D ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

Carbasugars; Glycosidase inhibitors; Hybrid sugars

Indexed keywords

SYNTHESIS (CHEMICAL);

CARBASUGARS; GLYCOSIDASE INHIBITORS; POLYHYDROXYLATED; STEREOSELECTIVE MANNER;

ORGANIC COMPOUNDS;

CARBASUGAR; FUSED HETEROCYCLIC RINGS; GLYCOPYRANOSIDE; GLYCOSIDASE INHIBITOR; GRIGNARD REAGENT; PYRAN DERIVATIVE;

ALLYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DIHYDROXYLATION; ENZYME SYNTHESIS; HYBRID; IC 50; INFRARED SPECTROMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 62549143527     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2009.01.017     Document Type: Article

References (39)

1. Arjona O., Gomez A.M., Lopez J.C., and Plumet J. Chem. Rev. 107 (2007) 1919-2036 and references therein
2. Plumet J., Gomez A.M., and Lopez J.C. Mini-Rev. Org. Chem. 4 (2007) 201-216
3. Clayden J., Parris S., Cabedo N.A., and Payne H. Angew. Chem., Int. Ed. 47 (2008) 5060-5062
4. Agrofoglio L., Suhas E., Farese A., Condom R., Challand S.R., Earl R.A., and Guedj R. Tetrahedron 50 (1994) 10611-10670
5. Suami T., and Ogawa S. Adv. Carbohydr. Chem. Biochem. 48 (1990) 21-90
6. Suami T. Top. Curr. Chem. 154 (1990) 257-283
7. Marquez V.E., and Lim M. Med. Res. Rev. 6 (1986) 1-40
8. Ogawa S. In: Chapleur Y. (Ed). Carbohydrate Mimics: Concepts and Methods (1998), Wiley-VCH, Weinheim 87-106
9. Ganem B. Acc. Chem. Res. 29 (1996) 340-347
10. Bols M. Acc. Chem. Res. 31 (1998) 1-8
11. Ogawa S., Uematsu Y., Yoshida S., Sasaki N., and Suami T. J. Carbohydr. Chem. 6 (1987) 471-478
12. Mehta G., and Ramesh S.S. Chem. Commun. (2000) 2429-2430
13. Schmidt D.D., Frommer W., Junge B., Muller W., Wingender W., Truscheit E., and Schafter D. Naturwissenschaften 64 (1977) 535-536
14. McClellan K., and Perry C.M. Drugs 61 (2001) 263-283
15. Albrecht S., Harrington P., Iding H., Karpf M., Trussardi R., Wirz B., and Zutter U. Chimia 58 (2004) 621-629
16. Kim C.U., Lew W., Williams M.A., Liu H., Zhang L., Swaminathan S., Bischofberger N., Chen M.S., Medel D.B., Tai C.Y., Laver G., and Stevens R.C. J. Am. Chem. Soc. 119 (1997) 681-690
17. Shing T.K.M., Cheng H.M., Wong W.F., Kwong C.S.K., Li J., Lau C.B.S., Leung P.S., and Cheng C.H.K. Org. Lett. 10 (2008) 3145-3148
18. Shing T.K.M., and Cheng H. Org. Lett. 10 (2008) 4137-4139
19. Shing T.K.M., Kwong C.S.K., Cheung A.W.C., Kok S.H.-L., Yu Z., Li J., and Cheng C.H.K. J. Am. Chem. Soc. 126 (2004) 15990-15992
20. Reddy B.G., and Vankar Y.D. Angew. Chem., Int. Ed. 44 (2005) 2001-2004
21. Jayakanthan K., and Vankar Y.D. Org. Lett. 7 (2005) 5441-5444
22. Jayakanthan K., and Vankar Y.D. Tetrahedron Lett. 49 (2006) 8667-8671
23. Rawal G.K., Rani S., kumar A., and Vankar Y.D. Tetrahedron Lett. 47 (2006) 9117-9120
24. Ramana D.V., and Vankar Y.D. Eur. J. Org. Chem. (2007) 5583-5589
25. Alam M.A., Kumar A., and Vankar Y.D. Eur. J. Org. Chem. (2008) 4972-4980
26. Ramana D.V., Kumar A., and Vankar Y.D. Tetrahedron 64 (2008) 9117-9122
27. Abrous L., Hynes Jr. J., Friedrich S.R., Smith III A.B., and Hirschmann R. Org. Lett. 3 (2001) 1089-1092
28. Abrous L., Jokiel P.K., Fridrich S.R., Hynes Jr. J., Smith III A.B., and Hirschmann R. J. Org. Chem. 69 (2004) 280-302
29. Carpintero M., Fernandez-Mayoralas A., and Jimenez-Barbero J. Eur. J. Org. Chem. (2001) 681-689
30. Lundt I., and Wagner S.H. J. Chem. Soc., Perkin Trans. 1 (2001) 780-788
31. Arjona O., Lorenzo G., Medel R., and Plumet J. Tetrahedron Lett. 42 (2001) 7041-7043
32. Arjona O., Iradier F., Medel R., and Plumet J. Tetrahedron: Asymmetry 10 (1999) 3431-3442
33. Cheshev P., Marra A., and Dondoni A. Carbohydr. Res. 341 (2006) 2714-2716
34. Allwein S.P., Cox J.M., Howard B.E., Johnson H.W.B., and Rainier J.D. Tetrahedron 58 (2002) 1997-2009
35. Cipolla L., Lay L., and Nicotra F. J. Org. Chem. 62 (1997) 6678-6681
36. Cleator E., McCusker C.F., Steltzer F., and Ley S.V. Tetrahedron Lett. 45 (2004) 3077-3080
37. Grubbs R.H. Handbook of Metathesis Vol. 2 (2003), Wiley-VCH, Weinheim Chapter 2
38. Sasaki M., Takeda N., Fuwa H., Watanabe R., Satake M., and Oshima Y. Tetrahedron Lett. 47 (2006) 5687-5691
39. Li Y.T., and Li S.C. In: Ginsberg V. (Ed). Methods in Enzymology (1972), Academic Press 702-713