Efficient regioselective O3-monodesilylation by hydrochloric acid in cyclodextrins. (17th June 2015)

• Record Type: Journal Article
• Authors: Gu, Jiamin; Chen, Tong; Wang, Qifang; Chen, Tieyu; Ling, Chang-Chun
• Is Part Of: Carbohydrate research. Volume 410(2015)
• Page Start: 36
• Page End: 46
• Publication Date: 2015-06-17
• Subjects: Cyclodextrins -- O3-Desilylation -- Silyl protecting group -- Hydrochloric acid -- Regioselectivity; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2015.04.003
• Languages: English
• ISSNs: 0008-6215

Abstract

Abstract: An efficient O3-monodesilylation method has been developed for the derivatization of per-3-O-silylated cyclodextrin (CD) derivatives. Using hydrochloric acid as a reagent, the O3-monodesilylation was found to be regioselective, mild, practical and general as it can be applied to all α-, β- and γ-CDs. The advantage of the methodology is that the acid-catalyzed O3-desilylation can be carried out in a stepwise manner so that different types of functional groups can be introduced to a CD molecule at different stage of the O3-desilylations. This makes the current methodology flexible and versatile. This current methodology constitutes one of the few methodologies available for the regioselective modification of CDs at the secondary face. Graphical abstract: Highlights: Per-3-O-silylated cyclodextrin substrates have been monodesilylated with HCl The methodology is generally applicable to all α-, β- and γ-cyclodextrins We further developed a stage-wise O3-desilylation methodology A strategy for multi-functionalization of cyclodextrins has been demonstrated