Synthesis of monofacially functionalized cyclodextrins bearing amino pendent groups

Dragos Vizitiu, Caroline S. Walkinshaw, Borio I. Gorin, Gregory R.J. Thatcher

Research output: Contribution to journalArticlepeer-review

66 Scopus citations

Abstract

Derivatives of the cyclodextrins, αCD, βCD, and ΥCD, in which all primary hydroxyls are substituted by amine pendant groups, may be synthesized efficiently from the per-6-bromo-6-deoxy-CD derivatives by direct reaction with amines. These ACD derivatives, which bear six, seven, or eight amine pendent groups, represent interesting biomimetic receptors and catalysts. The synthetic strategy relies on quantitative transformation and efficient purification as is demonstrated by preparation of 11 homogeneous ACD derivatives. The limitations of the synthesis and potential adaptations are illustrated by the synthesis of several more ACD derivatives to >95% purity. A synthetic route to a CD persubstituted with primary amine functionalities at the primary face, per-6-bromo-6-deoxy-CD, yields an alternative reagent to the simple per-6-bromo-6-deoxy-CD, which is more suitable for further synthetic transformations. The synthetic strategy is further adapted to preparation of a prototypical (6 + 1)-ACD derivative in which one primary position is substituted with a sulfide group and the remaining six primary face positions are substituted with amine pendent groups.

Original languageEnglish (US)
Pages (from-to)8760-8766
Number of pages7
JournalJournal of Organic Chemistry
Volume62
Issue number25
DOIs
StatePublished - 1997
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Synthesis of monofacially functionalized cyclodextrins bearing amino pendent groups'. Together they form a unique fingerprint.

Cite this