Premium
New chiral selectors: Design and synthesis of 6‐TBDMS‐2,3‐methyl β‐cyclodextrin 2‐2′ thioureido dimer and 6‐TBDMS‐2,3‐methyl (or 2‐methyl‐3‐acetyl) β‐cyclodextrin bearing an ( R ) mosher acid moiety
Author(s) -
Cravotto Giancarlo,
Bicchi Carlo,
Tagliapietra Silvia,
Costa Luisa,
Di Carlo Stefano,
Nervi Carlo
Publication year - 2004
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20069
Subject(s) - chemistry , moiety , cyclodextrin , chirality (physics) , dimer , stereochemistry , combinatorial chemistry , organic chemistry , chiral symmetry , physics , quantum mechanics , nambu–jona lasinio model , quark
Cyclodextrin (CD) derivatives are important selectors for analytical chiral recognition. Their enantioselectivities and chemical properties depend on ring size and on nature, number and location of substituents. This paper describes the synthesis of 6‐ O ‐TBDMS‐2,3‐ O ‐methyl β‐cyclodextrins bearing in position 2 either a single ( R )‐Mosher acid moiety or a second CD unit, in view of their possible application as chiral selectors. Most synthetic steps were successfully carried out under high‐intensity ultrasound using a new sonochemical reactor developed in the authors' laboratory. 6‐ O ‐TBDMS‐2‐ O ‐methyl‐3‐[( S )‐2‐methylbutyl]‐β‐CD was also synthesized and tested with gas chromatography; the enantiorecognition power of the other CD derivatives is also being tested. A computational study of model structures to design these CD derivatives. Chirality 16:526–533, 2004. © 2004 Wiley‐Liss, Inc.