REGIOSELECTIVE SYNTHESIS AND CHARACTERIZATION OF NAPHTHYLETHYLCARBAMOYL-BETA-CYCLODEXTRINS

被引：3

作者：

GAHM, KH ^{[1
]}

YOSHIDA, W ^{[1
]}

NIEMCZURA, WP ^{[1
]}

STALCUP, AM ^{[1
]}

机构：

[1] UNIV HAWAII MANOA,DEPT CHEM,HONOLULU,HI 96822

来源：

CARBOHYDRATE RESEARCH | 1993年 / 248卷

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/0008-6215(93)84120-U

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Regioselective reactions of 1-(1-naphthyl)ethyl isocyanate (NEIC) with beta-cyclodextrin (beta-CD) were studied with and without NaH activation of beta-CD in N,N-dimethylformamide (DMF) and pyridine. All six possible monosubstituted CD products were separated and characterized by proton NMR. Primary substitution product predominates when the reaction was carried out under reflux condition in pyridine without NaH activation. The C-2 substitution product predominates when the reaction was carried out in DMF. Conversion of 2-O-(1-(1-naphthyl)ethylcarbamoyl)-beta-CD to 6-O-(1-(1-naphthyl)ethylcarbamoyl)-beta-CD was observed when NaH was used to activate hydroxyl groups of CD.

引用

页码：119 / 128

页数：10

共 23 条

[1] CAPILLARY GAS-CHROMATOGRAPHIC SEPARATION OF ENANTIOMERS WITH STABLE DIPENTYL-ALPHA-CYCLODEXTRIN-DERIVATIZED, BETA-CYCLODEXTRIN-DERIVATIZED AND GAMMA-CYCLODEXTRIN-DERIVATIZED STATIONARY PHASES [J].