Synthesis, Table of Contents SHORTPAPER© Georg Thieme Verlag Stuttgart · New YorkFacile One-Step Synthesis of Mono-2-(p-Tolylsulfonyl)-β-cyclodextrin under Aqueous ConditionsMichael Strerath, Martin Meng, Stefan Kubik*Technische Universität Kaiserslautern, Fachbereich Chemie - Organische Chemie, Erwin-Schrödinger-Strasse, 67663 Kaiserslautern, GermanyFax: +49(631)2053921; e-Mail: kubik@chemie.uni-kl.de; Recommend Article Abstract Buy Article All articles of this category 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%. Key words cyclodextrins - sulfonates - regioselectivity - host-guest systems Full Text References References <A NAME="RT14706SS-1A">1a</A> Wenz G. Angew. Chem., Int. Ed. Engl. 1994, 33: 803 ; Angew. Chem. 1994, 106, 851 <A NAME="RT14706SS-1B">1b</A> See also the special issue on cyclodextrin chemistry: Chem. Rev. 1998, 98: 1741 <A NAME="RT14706SS-2A">2a</A> Breslow R. Pure Appl. Chem. 1994, 66: 1573 <A NAME="RT14706SS-2B">2b</A> Breslow R. Acc. Chem. Res. 1995, 28: 146 <A NAME="RT14706SS-3">3</A> Hedges AR. Chem. Rev. 1998, 98: 2035 <A NAME="RT14706SS-4">4</A> Easton CJ. Lincoln SF. Modified Cyclodextrins Imperial College Press; London: 1999. <A NAME="RT14706SS-5A">5a</A> Takahashi K. Hattori K. Toda F. Tetrahedron Lett. 1984, 25: 3331 <A NAME="RT14706SS-5B">5b</A> Petter RC. Salek JS. Sikorski CT. Kumaravel G. Lin FT. J. Am. Chem. Soc. 1990, 112: 3860 <A NAME="RT14706SS-6">6</A> Rong D. D’Souza VT. Tetrahedron Lett. 1990, 31: 4275 <A NAME="RT14706SS-7">7</A> Murakami T. Harata K. Morimoto S. Tetrahedron Lett. 1987, 28: 321 <A NAME="RT14706SS-8A">8a</A> Pregel MJ. Buncel E. Can. J. Chem. 1991, 69: 130 <A NAME="RT14706SS-8B">8b</A> 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 <A NAME="RT14706SS-8C">8c</A> Venema F. Nelissen HFM. Berthault P. Birlirakis N. Rowan AE. Feiters MC. Nolte RJM. Chem. Eur. J. 1998, 4: 2237 <A NAME="RT14706SS-9A">9a</A> Gelb RI. Schwartz LM. Bradshaw JJ. Laufer DA. Bioorg. Chem. 1980, 9: 299 <A NAME="RT14706SS-9B">9b</A> Gelb RI. Schwartz LM. Laufer DA. Bioorg. Chem. 1982, 11: 274 <A NAME="RT14706SS-10">10</A> Gelb RI. Schwartz LM. Radeos M. Edmonds RB. Laufer DA. J. Am. Chem. Soc. 1982, 104: 6283 <A NAME="RT14706SS-11">11</A> The response factor of the RI detector for both compounds was determined independently and is close to 1. <A NAME="RT14706SS-12">12</A> Ueno A. Breslow R. Tetrahedron Lett. 1982, 23: 3451