Practical de-O-acylation reactions promoted by molecular sieves

Carbohydrate Research

Volumn 339, Issue 3, 2004, Pages 729-732

  Kartha, K P Ravindranathan ^a   Mukhopadhyay, Balaram ^b   Field, Robert A ^b  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

^b UNIVERSITY OF EAST ANGLIA   (United Kingdom)

Author keywords

Alcohols; Deacetylation; Molecular sieves

Indexed keywords

ACYLATION; DERIVATIVES; METHANOL; MOLECULAR SIEVES;

TRANSFER REACTIONS;

POLYSACCHARIDES;

BENZOIC ACID; CARBOHYDRATE DERIVATIVE; METHANOL; N ACETYLGLUCOSAMINE; OXYGEN;

ACCURACY; ACYLATION; ARTICLE; CARBOHYDRATE SYNTHESIS; CHEMICAL REACTION KINETICS; DESICCATION; DRY POWDER; ISOMER; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; MOLECULAR MECHANICS; PRIORITY JOURNAL; REACTION ANALYSIS; SIEVE TUBE; TECHNIQUE;

EID: 0842309174     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2003.11.021     Document Type: Article

References (16)

1. Breck D.W., Eversole W.G., Milton R.M., Reed T.B., Thomas T.L. J. Am. Chem. Soc. 78:1956;5963-5971. and references cited therein.
2. Aldrich Technical Information Bulletin, No. AL-143, Sigma-Aldrich Publication. http://www.sigmaaldrich.com/Brands/Aldrich/Technical_Bulletins/ AL_143/Molecular_Sieves.html.
3. Vogel A.I. Vogel's Text Book of Practical Organic Chemistry. 4th ed. 1978;Longman Group Limited, London.
4. Pellets (1.6 mm), supplied by Aldrich, UK (Catalogue no 33,430-8).
5. An aqueous slurry (5%) of 4 Å molecular sieves, 4-8 mesh, supplied by Aldrich, UK (Catalogue no 20,859-0), has been reported to have a pH value of 10.5 (see Ref. 2).
6. Fieser L.F., Fieser M. Reagents for Organic Synthesis. 1967;John Wiley and Sons, New York.
7. Mizuno M., Kobayashi K., Nakajima H., Koya M., Inazu T. Synth. Commun. 32:2002;1665-1670.
8. Adinolfi M., Barone G., Iadonisi A., Schiattarella M. Tetrahedron Lett. 44:2003;4661-4663.
9. 2 both 3 or 4 Å powdered molecular sieves proved effective in de-O-acetylation reactions, although reactions employing the former were noticeably slower.
10. Grundler G., Schmidt R.R. Liebigs Ann. Chem. 1984;1826-1847.
11. Pozsgay V., Coxon B. Carbohydr. Res. 277:1995;171-178.
12. Kartha K.P.R., Field R.A. Tetrahedron. 53:1997;11753-11766. and references cited therein.
13. Fletcher H.G. Whistler R.L., Wolfrom M.L. Methods in Carbohydrate Chemistry. Vol. II:1963;228-230 Academic, New York and London. and references cited therein.
14. Demchenko A.V., Boons G.J. J. Org. Chem. 66:2001;2547-2554.
15. Vegad H., Gray C.J., Somers P.J., Dutta A.S. J. Chem. Soc., Perkin Trans. 1. 1997;1429-1441.
16. Lazarevic D., Thiem J. Carbohydr. Res. 337:2002;2187-2194.