Triphenylphosphine Polymer-Bound/Iodine Complex: A Suitable Reagent for the Preparation of O-Isopropylidene Sugar Derivatives

Abstract

O-Isopropylidene derivatives of sugars are readily prepared by using the Lewis acid and dehydrating agent triphenylphosphine polymer-bound/I₂ complex. This new method is characterized by smooth, non-equilibrating reaction conditions and a very clean, simple work-up, making it particularly suitable for O-isopropyliden­ation of sugars under mild conditions and with low environmental impact.

Key words

acetals - carbohydrates - triarylphosphine-iodine complex - O-isopropylidene - acetonation

References

• 1 Goi A. Bruzzese T. Notarianni AF. Riva M. Ronchini A. Arzneim. Forsch./Drug Res.  1979,  7:  986 
• 2a Stevens JD. Chem. Commun.  1969,  1140 
• 2b Hughes NA. Speakman PRH. Carbohydr. Res.  1965,  1:  171 
• 3 Schmidt OT. Meth. Carbohydr. Chem.  1963,  2:  318 
• 4a Nair PRM. Shah PM. Sreenivasan B. Starch  1981,  33:  384 
• 4b Nikiforov VA. Zarutsski VV. Chapanov ID. Vasil’eva IB. Dolgushina NN. Khim.-Farm. Zh.  1982,  16:  1102 ; Chem. Abstr. 1982, 97, 215482x
• 5a Mongenlie S. Acta Chem. Scand.  1973,  27:  3609 
• 5b Mongenlie S. Acta Chem. Scand., Ser. B  1975,  297:  367 
• 6 Kartha KPR. Tetrahedron Lett.  1986,  27:  3415 
• 7 Singh PP. Gharia MM. Dasgupta F. Srivastava HC. Tetrahedron Lett.  1977,  439 
• 8 Pfaff PK, Paust J, and Hartmann H. inventors; Ger. Offen, DE  3505150.  ; Chem. Abstr. 1985, 106, 18984r
• 9 Lal B. Gidwani RM. Rupp RH. Synthesis  1989,  711 
• 10 Rauter AP. Ramoa-Ribeiro F. Fernandes AC. Figueiredo JA. Tetrahedron  1995,  51:  6529 
• 11 Meskens FAJ. Synthesis  1981,  501 
• 12a Catelani G. Colonna F. Marra A. Carbohydr. Res.  1988,  182:  297 
• 12b Gelas J. Horton D. Heterocycles  1981,  16:  1587 
• 13 Leadbeater NE. Marco M. Chem. Rev.  2002,  102:  3217 
• 14 Dewry DH. Coe DM. Poon S. Med. Res. Rev.  1999,  19:  97 
• 15 Caputo R. Ferreri C. Noviello S. Palumbo G. Synthesis  1986,  499 
• 16a Bernard M. Ford WT. J. Org. Chem.  1983,  48:  326 
• 16b Regen SL. Lee DP. J. Org. Chem.  1975,  40:  1669 
• 18 Stacey BE. Tierney B. Carbohydr. Res.  1976,  49:  129 
• 19 Martin OR. Korppi-Tommola S.-L. Szare WA. Can. J. Chem.  1982,  60:  1857 
• 20 May JA. Sartorelli AC. J. Med. Chem.  1979,  22:  971 ; and references cited therein
• 21a Shaikh NS. Bhor SS. Gajare AS. Deshpande VH. Wakharkar RD. Tetrahedron Lett.  2004,  45:  5395 
• 21b Moon HR. Choi WJ. Kim HO. Jeong LS. Tetrahedron: Asymmetry  2002,  13:  1189 
• 21c Asakura J. Matsubara Y. Yoshihara M. J. Carbohydr. Chem.  1996,  15:  231 
• 22 von Reichstein T. Grüssner A. Helv. Chim. Acta  1934,  17:  311 
• 23 Pressman BC. Anderson L. Lardy HA. J. Am. Chem. Soc.  1950,  72:  2404 ; references cited therein

17

Triphenylphosphine-iodine complex showed the same reactivity of the polymer bound/iodine complex towards all the tested sugars.