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Capping α‐Cyclodextrin with Cyclotriveratrylene by Triple Disulfide‐Bridge Formation
Author(s) -
Brégier Frédérique,
Lavalle Juliette,
Chambron JeanClaude
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201729
Subject(s) - chemistry , diastereomer , dimer , cyclodextrin , disulfide bond , stereochemistry , yield (engineering) , derivative (finance) , medicinal chemistry , organic chemistry , biochemistry , materials science , economics , financial economics , metallurgy
Disulfide‐bond formation is an expeditious coupling reaction to make macropolycyclic symmetrical receptors. It is used here for the preparation of unsymmetrical cavitands based on α‐cyclodextrin (α‐CDX) and cyclotriveratrylene (CTV) analogues. Accordingly, diastereomeric hemicryptophanes 2a and 2b were obtained in 11 % isolated yield by the iodine oxidation of a 1:1 mixture of racemic cyclotrithiophenolene ( 3 ) and the C 3 ‐symmetric trithiol derivative of permethylated α‐cyclodextrin (PM α‐CDX) 4 . Remarkably, the target hemicryptophanes were obtained in a 5:3 diastereomeric ratio. The reaction produced mainly (34 %) a singly disulfide‐bridged PM α‐CDX dimer 7 , however no traces of triply disulfide‐bridged head‐to‐head PM α‐CDX dimer were detected. In addition, the formation of the known S ‐cryptophane‐0.0.0 was observed.