Amplification of the reactivity difference between two methylene groups of cyclodextrins via a cap

被引：26

作者：

Yuan, DQ ^{[1
]}

Yamada, T ^{[1
]}

Fujita, K ^{[1
]}

机构：

[1] Nagasaki Univ, Fac Pharmaceut Sci, Nagasaki 8528521, Japan

来源：

CHEMICAL COMMUNICATIONS | 2001年 / 24期

关键词：

D O I：

10.1039/b108416j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel concept has been established for making heterodisubstituted cyclodextrin derivatives. Upon treatment with imidazole, 6(A),6(B)-mesitylenedisulfonyl-capped beta -cyclodextrin 1 demonstrated a reactivity about 10 times higher at the 6(B) position than at the 6(A) position, leading to the selective formation of hetero-disubstituted cyclodextrins 3.

引用

页码：2706 / 2707

页数：2

共 16 条

[1] Biomimetic reactions catalyzed by cyclodextrins and their derivatives [J].

Breslow, R ;

Dong, SD .

CHEMICAL REVIEWS, 1998, 98 (05) :1997-2011

[2] THE COPPER(II) COMPLEX WITH THE IMIDAZOLE-BOUND HISTAMINE DERIVATIVE OF BETA-CYCLODEXTRIN AS A POWERFUL CHIRAL DISCRIMINATING AGENT [J].

CUCINOTTA, V ;

DALESSANDRO, F ;

IMPELLIZZERI, G ;

VECCHIO, G .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (23) :1743-1745

[3] Reversal of optical induction in transamination by regioisomeric bifunctionalized cyclodextrins [J].

Fasella, E ;

Dong, SD ;

Breslow, R .

BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (05) :709-714

[4] ENZYME-BASED DISCRIMINATION BETWEEN CLOCKWISE AND COUNTER-CLOCKWISE ISOMERS OF UNSYMMETRICALLY DISUBSTITUTED BETA-CYCLODEXTRINS - 6A, 6B-DERIVATIVES AND 6A, 6G-DERIVATIVES [J].

FUJITA, K ;

MATSUNAGA, A ;

IKEDA, Y ;

IMOTO, T .

TETRAHEDRON LETTERS, 1985, 26 (52) :6439-6442

[5] A COMPLETE SET OF 6A-AZIDO-6A-DEOXY-6X-O-SULFONYL-BETA-CYCLODEXTRINS [J].

FUJITA, K ;

YAMAMURA, H ;

EGASHIRA, Y ;

IMOTO, T .

TETRAHEDRON LETTERS, 1992, 33 (24) :3511-3514

[6] 6A6B, 6A6C, AND 6A6D-DITOSYLATES OF BETA-CYCLODEXTRIN [J].

FUJITA, K ;

MATSUNAGA, A ;

IMOTO, T .

TETRAHEDRON LETTERS, 1984, 25 (48) :5533-5536

[7] A COMPLETE SET OF BETA-CYCLODEXTRINS-6A, 6X-DIACTIVATED BY 2 DIFFERENT SULFONYL GROUPS [J].

FUJITA, K ;

YAMAMURA, H ;

IMOTO, T .

TETRAHEDRON LETTERS, 1991, 32 (46) :6737-6740

[8]

FUJITA K, 1987, J ORG CHEM, V52, P63

[9] Synthesis and fluorescent molecular sensing at exciplex emission of pyrene- and cyanobenzene-modified γ-cyclodextrins [J].

Hamada, F ;

Narita, M ;

Kinoshita, K ;

Makabe, A ;

Osa, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2001, Royal Society of Chemistry (03) :388-394

[10] Methods for selective modifications of cyclodextrins [J].

Khan, AR ;

Forgo, P ;

Stine, KJ ;

D'Souza, VT .

CHEMICAL REVIEWS, 1998, 98 (05) :1977-1996

← 1 2 →