New chiral selectors: design and synthesis of 6-TBDMS-2,3-methyl beta-cyclodextrin 2-2' thioureido dimer and 6-TBDMS-2,3-methyl (or 2-methyl-3-acetyl) beta-cyclodextrin bearing an (R) Mosher acid moiety.
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 beta-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]-beta-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.
Università di Torino, Dipartimento di Scienza e Tecnologia del Farmaco, Turin, Italy.
Giancarlo
G
Cravotto
Carlo
C
Bicchi
Silvia
S
Tagliapietra
Luisa
L
Costa
Stefano
S
Di Carlo
Carlo
C
Nervi
D000478:Alkylation; D003505:Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry*; D019281:Dimerization; D015195:Drug Design; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D010648:Phenylacetates / Q000138:chemical synthesis / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism; D013890:Thiourea / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*
C492684:6-O-tert-butyldimethylsilyl-2,3-methyl beta-cyclodextrin 2-2' thioureido dimer; D003505:Cyclodextrins; D017646:Organosilicon Compounds; D010648:Phenylacetates; D012821:Silanes; C103256:tert-butyldimethylsilane; C108322:Mosher's acid; D013890:Thiourea