Facile One-Step Synthesis of Mono-2-(p-Tolylsulfonyl)-β-cyclodextrin under Aqueous Conditions

Abstract

A new and convenient method is presented for the synthesis of mono-2-(p-tolylsulfonyl)-β-cyclodextrin under aqueous conditions that does not require large amounts of polar organic solvents such as DMF, metal-containing reagents such as dibutyltin oxide, or flammable bases such as NaH. Yields are typically around 20%.

cyclodextrins - sulfonates - regioselectivity - host-guest systems

References

1a Wenz G. Angew. Chem., Int. Ed. Engl.  1994,  33:  803 ; Angew. Chem. 1994, 106, 851

1b See also the special issue on cyclodextrin chemistry: Chem. Rev.  1998,  98:  1741 

2a Breslow R. Pure Appl. Chem.  1994,  66:  1573 

2b Breslow R. Acc. Chem. Res.  1995,  28:  146 

3 Hedges AR. Chem. Rev.  1998,  98:  2035 

4 Easton CJ. Lincoln SF. Modified Cyclodextrins   Imperial College Press; London: 1999. 

5a Takahashi K. Hattori K. Toda F. Tetrahedron Lett.  1984,  25:  3331 

5b Petter RC. Salek JS. Sikorski CT. Kumaravel G. Lin FT. J. Am. Chem. Soc.  1990,  112:  3860 

6 Rong D. D’Souza VT. Tetrahedron Lett.  1990,  31:  4275 

7 Murakami T. Harata K. Morimoto S. Tetrahedron Lett.  1987,  28:  321 

8a Pregel MJ. Buncel E. Can. J. Chem.  1991,  69:  130 

8b van Dienst E. Snellink BHM. von Piekartz I. Grote-Gansey MHB. Venema F. Feiters MC. Nolte RJM. Engbersen JFJ. Reinhoudt DN. J. Org. Chem.  1995,  60:  6537 

8c Venema F. Nelissen HFM. Berthault P. Birlirakis N. Rowan AE. Feiters MC. Nolte RJM. Chem. Eur. J.  1998,  4:  2237 

9a Gelb RI. Schwartz LM. Bradshaw JJ. Laufer DA. Bioorg. Chem.  1980,  9:  299 

9b Gelb RI. Schwartz LM. Laufer DA. Bioorg. Chem.  1982,  11:  274 

10 Gelb RI. Schwartz LM. Radeos M. Edmonds RB. Laufer DA. J. Am. Chem. Soc.  1982,  104:  6283 

11

The response factor of the RI detector for both compounds was determined independently and is close to 1.

12 Ueno A. Breslow R. Tetrahedron Lett.  1982,  23:  3451