Enhanced single-isomer separation and pseudoenantiomer resolution of new primary rim heterobifunctionalized α-cyclodextrin derivatives.

ABSTRACT: The synthesis of batch-to-batch reproducible cyclodextrin (CD) derivatives often requires functionalization at specific positions of the CD skeleton. However, the regioselective preparation of this type of CD derivatives remains a challenge in synthetic chemistry. Thus, the present study aimed to prepare all positional regioisomers on the primary rim of homobifunctionalized diazido-α-CDs by selective substitution on the primary rim. Specifically, three positional regioisomers 6^A,6^B-, 6^A,6^C-, and 6^A,6^D-diazido-α-CDs were prepared via different intermediates (using sulfonylation with capping agents, bromination and tosylation). Furthermore, heterobifunctionalized 6^A-azido-6^X-mesitylenesulfonyl-α-CDs were

SUBMITTER: Ticha I 

PROVIDER: S-EPMC6244315 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature