Sulfuric acid immobilized on silica: an efficient reusable catalyst for selective hydrolysis of the terminal O-isopropylidene group of sugar derivatives

Tetrahedron Letters

Volumn 47, Issue 39, 2006, Pages 6987-6991

  Rajput, Vishal Kumar ^a   Roy, Bimalendu ^a   Mukhopadhyay, Balaram ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE; SILICON DIOXIDE; SULFURIC ACID;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ECONOMIC ASPECT; HYDROLYSIS; SYNTHESIS;

EID: 33747772110     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.07.125     Document Type: Article

References (25)

1. Garegg P.J. Adv. Carbohydr. Chem. Biochem. 59 (2004) 69-134
2. In: Osborn H.M.I. (Ed). Best Synthetic Methods: Carbohydrates (2003), Academic Press, London
3. Fleet G.W.J., and Smith P.W. Tetrahedron Lett. 26 (1985) 1469-1472
4. Gerspacher M., and Rapoport H. J. Org. Chem. 56 (1991) 3700-3705
5. Yadav J.S., Chander M.C., and Reddy K.K. Tetrahedron Lett. 33 (1992) 135-138
6. Manna S., Jacques Y.P., and Falck J.R. Tetrahedron Lett. 27 (1986) 2679-2682
7. Lablance Y., Fitzsimmons J., Adams E.P., and Rokacha J. J. Org. Chem. 51 (1986) 789-793
8. Vijayasaradhi S., Singh J., and Aidhan I.S. Synlett (2000) 110-112
9. Iwata M., and Ohrui H. Bull. Chem. Soc. Jpn. 54 (1981) 2837
10. Xiao X., and Bai D. Synlett (2001) 535
11. Venkateswarlu Y., and Swamy R.S. Tetrahedron Lett. 43 (2002) 7549-7552
12. Park K.H., Yoon Y.J., and Lee S.G. Tetrahedron Lett. 35 (1994) 9737-9740
13. Majumder S., and Bhattacharyya A. J. Org. Chem. 64 (1999) 5682-5685
14. Kim K.S., Song Y.H., Lee B.H., and Hahn C.S. J. Org. Chem. 51 (1986) 404-407
15. Mahender G., Ramu R., Ramesh C., and Das B. Chem. Lett. 32 (2003) 734-735
16. Agarwal A., and Vankar Y.D. Carbohydr. Res. 340 (2005) 1661-1667
17. Zolfigol M.A., and Bamoniri A. Synlett (2002) 1621-1623
18. Zolfigol M.A. Tetrahedron 57 (2001) 9509
19. Zolfigol M.A., Shirini F., Ghorbani Choghamarani A., and Mohammadpoor-Baltork I. Green Chem. 4 (2002) 562
20. Shirini F., Zolfigol M.A., and Mohammadi K. Bull. Korean Chem. Soc. 25 (2004) 325-327
21. Mukhopadhyay B. Tetrahedron Lett. 47 (2006) 4337-4341
22. Rajput V., and Mukhopadhyay B. Tetrahedron Lett. 47 (2006) 5939-5941
23. 4-silica which was then dried at 110 °C for 3 h.
24. 2 (2 mL) and the filtrate was evaporated in vacuo. The compound thus obtained was sufficiently pure for further use (NMR and mass spectrometry). For the mannose derivative only, the crude product was purified by column chromatography using n-hexane-EtOAc (1:1).
25. 13C NMR spectra are available in the Supplementary data.