2A,3A-Alloepithio-2A,3A-dideoxy-β-cyclodextrin: synthesis and application in the construction of rigid elliptical cavities with functionality at the secondary hydroxyl side

Autor:	Hidetoshi Morikawa, Kahee Fujita, De-Qi Yuan, Makoto Fukudome, Yuji Okabe, Toshihiro Fujioka, Madoka Sakaguchi
Rok vydání:	2004
Předmět:	chemistry.chemical_classification Cyclodextrin biology Artificial enzyme Organic Chemistry Biochemistry chemistry.chemical_compound Thiourea chemistry Thiirane Yield (chemistry) Drug Discovery Polymer chemistry Thiol biology.protein Surface modification Episulfide
Zdroj:	Tetrahedron Letters. 45:9045-9048
ISSN:	0040-4039
Popis:	2 A ,3 A -Alloepithio-2 A ,3 A -dideoxy-β-cyclodextrin ( 2 ), which may serve as a novel and important intermediate for the functionalization of the secondary face of β-cyclodextrin, was prepared in 40% yield by heating 2 A ,3 A -mannoepoxy-β-cyclodextrin and thiourea in water. Treatment of 2 with AgNO 3 in the presence of amines afforded 3 A ,6 A -anhydro-2 A -deoxy-2 A -thio-β-cyclodextrin ( 4 ) in 73% yield. The latter is an artificial enzyme candidate with a specifically orientated thiol group and a rigid elliptical cavity.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::22728162b451f0c947c079b7d3042cc3 https://doi.org/10.1016/j.tetlet.2004.10.031 Zobrazit plný text záznamu Full Text from ScienceDirect