Formation of amphiphilic cyclodextrins via hydrophobic esterification at the secondary hydroxyl face

Optimization of entrapment of metronidazole in amphiphilic β-cyclodextrin nanospheres

“…Hexanoyl-␤-cyclodextrin ester (␤-CD-C 6 ) was obtained by a synthetic route [10]. The synthesis was realized in three steps and briefly consists in the protection of the primary hydroxyl groups at the O6 position by the t-butyldimethylchlorosilane (TBDM) (Fluka Chemie AG, St-Quentin Fallavier, France) in dry pyridine.…”

Les cyclodextrines amphiphiles et leurs applications. Élaboration de nanoparticules de cyclodextrines amphiphiles pour des applications biomédicales

“…D'autres CD totalement substituées par des chaînes lipophiles sur la face secondaire ont été décrites par Memisoglu et al [5] et utilisées en tant que nanoparticules pour l'encapsulation. Les cyclodextrines « type Jupe », persubstituées sur la face secondaire, sont obtenues quant à elles en trois étapes à partir de la CD native, impliquant une étape de protection des hydroxyles primaires, une acylation des hydroxyles secondaires par un chlorure ou anhydride d'acide, et enfin une déprotection des hydroxyles primaires [6].…”

Efficient and Versatile Modification of the Secondary Face of Cyclodextrins through Copper‐Catalyzed Huisgen 1,3‐Dipolar Cycloaddition

“…To achieve regioselectivity, the primary face is selectively protected, usually with a bulky group, most commonly the tertbutyldimethylsilyl (TBDMS) [33] and thexyldimethylsilyl groups, [34] to allow subsequent chemical modifications at the secondary face. The most common transformations performed on the secondary face are either acylation by reacting per-6-O-protected CDs with a desired acylating reagent, [35,36] or alkylation under Williamson ether synthesis conditions. [37][38][39] Acylation has proven to be the most efficient method to introduce aliphatic chains of various lengths to the secondary face.…”