Unusual regioselective acylation of the primary hydroxy groups of β-cyclodextrin

Unusual regioselective acylation of the primary hydroxy groups of β-cyclodextrin Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2003, Volume: 52, Number: 1, Pages: 237-246 Pages count : 10 DOI: 10.1023/a:1022485407440

Authors

Glazyrin A.E. ¹ , Syrtsev A.N. ¹ , Kurochkina G.I. ¹ , Kononov L.O. ² , Grachev M.K. ¹ , Nifant"ev E.E. ¹

Affiliations

1	Moscow Pedagogical State University, 3 per. Nesvizhsky, 119021, Moscow, Russian Federation
2	N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

The reaction of β-cyclodextrin (1) with palmitoyl (2) and valeryl (4) chlorides in DMF or Py, unlike previously studied acetylation of 1, involves only the primary hydroxy groups of 1. The outcome of the reaction depends on the reaction conditions and the nature of the acid scavenger used (Et3N, Pri 2NEt, PhNMe2, Py). 13C NMR spectroscopy was shown to be an effective tool in determining the number and position of aliphatic carboxylic acid residues introduced into 1. A hypothesis stating that preliminary formation of a reactive inclusion complex (acid chloride⊂1) is required for the acylation of 1 to occur is proposed and substantiated. This hypothesis provides a unified explanation for a variety of unusual facts observed in the acylation of 1 and its derivatives.

Glazyrin A.E. , Syrtsev A.N. , Kurochkina G.I. , Kononov L.O. , Grachev M.K. , Nifant"ev E.E.
Unusual regioselective acylation of the primary hydroxy groups of β-cyclodextrin
Russian Chemical Bulletin. 2003. V.52. N1. P.237-246. DOI: 10.1023/a:1022485407440 WOS Scopus OpenAlex

Web of science:	WOS:000181542300035
Scopus:	2-s2.0-0037287776
OpenAlex:	W2951338188

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OpenAlex	8
Scopus	8
Web of science	9