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

Cui Yanli; Mao Yangyi; Mao Jianwei; Zhang Yongmin

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

机译：朝着单氧化物6-羟基α-环糊精两亲型衍生物的智能区域选择性

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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 alpha-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 C-4-C-6 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.

机译：遵循环保发展的趋势，本文描述了一种智能区域选择性修饰，对于α-环糊精的原代面前的单羟基 - 羟基和五羟基 - 烷基共存，没有额外的催化作用或没有酶工艺，仅通过调节碱与烷基化剂的比例，产率良好。该新方法最小化了繁琐的保护，脱保护步骤，并为进一步的尖端研究提供了有用的中间体。因此，绿色和经济进入的范围从五戊烯酯取代到C-4-C-6烷基取代的延伸。推测，该机制可以通过系统中碱的浓度和亲电试剂RBR的空间效应来控制。

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来源
《RSC Advances》 |2020年第18期|共8页
作者
Cui Yanli; Mao Yangyi; Mao Jianwei; Zhang Yongmin;
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作者单位

Sorbonne Univ CNRS Inst Parisien Chim Mol UMR 8232 4 Pl Jussieu F-75005 Paris France;

Hangzhou Yanqing Biotechnol Co Ltd Hangzhou 310052 Peoples R China;

Zhejiang Univ Sci &

Technol Hangzhou 310013 Peoples R China;

Sorbonne Univ CNRS Inst Parisien Chim Mol UMR 8232 4 Pl Jussieu F-75005 Paris France;

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正文语种 eng
中图分类化学;
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1. Smart regioselectivity towards mono 6-hydroxyl alpha-cyclodextrin amphiphilic derivatives [J] . Cui Yanli, Mao Yangyi, Mao Jianwei, RSC Advances . 2020,第18期

机译：朝着单氧化物6-羟基α-环糊精两亲型衍生物的智能区域选择性
2. Control of the regioselectivity for new fluorinated amphiphilic cyclodextrins: Synthesis of di- and tetra(6-deoxy-6-alkylthio)- and 6-(perfluoroalkypropanethio)-alpha-cyclodextrin derivatives [J] . Bertino-Ghera B, Perret F, Fenet B, The Journal of Organic Chemistry . 2008,第18期

机译：新的氟化两亲环糊精的区域选择性的控制：二和四（6-脱氧-6-烷硫基）-和6-（全氟烷基丙烷硫基）-α-环糊精衍生物的合成
3. Novel nanoparticles made from amphiphilic perfluoroalkyl alpha-cyclodextrin derivatives: preparation, characterization and application to the transport of acyclovir. [J] . Ghera BB, Perret F, Chevalier Y International Journal of Pharmaceutics . 2009,第1a2期

机译：由两亲性全氟烷基α-环糊精衍生物制成的新型纳米颗粒：无环鸟苷的制备，表征和应用。
4. Optical resolution of racemic compounds by chiral HPLC on immobilized amylose derivatives with regioselective substituents [C] . Shen Jun, Liu Shuangyan, Li Pengfei, 2011 IEEE/ICME International Conference on Complex Medical Engineering . 2011

机译：通过手性HPLC在具有区域选择性取代基的固定直链淀粉衍生物上光学拆分外消旋化合物
5. Synthesis of polyisoprene and polyisoprene-containing amphiphilic block copolymers via RAFT for the preparation of nanoparticles with regioselective functional domains [D] . Germack, David Sam 2007

机译：通过RAFT合成聚异戊二烯和含聚异戊二烯的两亲嵌段共聚物，用于制备具有区域选择性功能域的纳米粒子
6. Regioselective decarboxylative addition of malonic acid and its mono(thio)esters to 4-trifluoromethylpyrimidin-2(1H)-ones [O] . Sergii V Melnykov, Andrii S Pataman, Yurii V Dmytriv, 2017

机译：丙二酸及其单（硫）酯的区域选择性脱羧加成至4-三氟甲基嘧啶-2（1H）-ones
7. Molecular arrangements and photoisomerizarion of amphiphilic azobenzene derivatives in mono- and multilayers. [O] . Hiroo NAKAHARA, Kiyoshige FUKUDA, Masatsugu SIMOMURA, 1988

机译：单双层含有两亲亚偶氮苯衍生物的分子布置和光学蛋白。

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

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