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Issue 18, 2020, Issue in Progress
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Smart regioselectivity towards mono 6-hydroxyl α-cyclodextrin amphiphilic derivatives

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Abstract

Following the trend of eco-friendly development, a smart regioselective modification is described herein, for mono 6-hydroxyl and penta-alkyl coexistence on the primary face of α-cyclodextrins with no additional catalysis or no enzyme process, just via the adjustment of the ratio of alkali to alkylation agent, with good yields. The novel procedure minimized the tedious protection, deprotection steps and provided useful intermediates for further cutting edge research. Thus, the scope of green and economical access is extended from penta-pentenyl substitution to C4–C6 alkyl group substitution. It was speculated that the mechanism might be controlled by the concentration of alkali in the system and the steric effects of the electrophilic reagent RBr.

Graphical abstract: Smart regioselectivity towards mono 6-hydroxyl α-cyclodextrin amphiphilic derivatives

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Supplementary files

Article information


Submitted
11 Jan 2020
Accepted
10 Feb 2020
First published
13 Mar 2020

This article is Open Access

RSC Adv., 2020,10, 10695-10702
Article type
Paper

Smart regioselectivity towards mono 6-hydroxyl α-cyclodextrin amphiphilic derivatives

Y. Cui, Y. Mao, J. Mao and Y. Zhang, RSC Adv., 2020, 10, 10695
DOI: 10.1039/D0RA00299B

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