BETA-CYCLOALTRIN - A CYCLOOLIGOSACCHARIDE CONSISTING OF 7 ALPHA(1-]4)-LINKED ALTROPYRANOSES

被引:33
作者
FUJITA, K [1 ]
SHIMADA, H [1 ]
OHTA, K [1 ]
NOGAMI, Y [1 ]
NASU, K [1 ]
KOGA, T [1 ]
机构
[1] DAIICHI COLL PHARMACEUT SCI,TOKYO,JAPAN
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1995年 / 34卷 / 15期
关键词
ALTROSE; BETA-CYCLOALTRIN; CYCLODEXTRINS; OLIGOSACCHARIDES;
D O I
10.1002/anie.199516211
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A surprisingly simple approach—heating per‐2,3‐anhydro‐(2S)‐β‐cyclodextrin in water at reflux—provides the novel cyclooligosaccharide β‐cycloaltrin (1) in 73% yield. In this one‐step hydrolysis, ring opening results in the altro configuration in every sugar unit. The inclusion properties of 1 should be interesting. (Figure Presented.) Copyright © 1995 by VCH Verlagsgesellschaft mbH, Germany
引用
收藏
页码:1621 / 1622
页数:2
相关论文
共 12 条
[1]   EQUILIBRIA BETWEEN PYRANOSES AND FURANOSES .2. ALDOSES [J].
ANGYAL, SJ ;
PICKLES, VA .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1972, 25 (08) :1695-&
[2]   COMPOSITION AND CONFORMATION OF SUGARS IN SOLUTION [J].
ANGYAL, SJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1969, 8 (03) :157-&
[3]  
ANGYAL SJ, 1969, ANGEW CHEM, V81, P172
[4]   Synthesis and properties of cyclo-alpha-1,4-manno-2,3-epoxides [J].
Coleman, Anthony W. ;
Zhang, Ping ;
Ling, Chang-Chun ;
Mahuteau, Jacqueline ;
Parrot-Lopez, Helene ;
Miocque, Marcel .
SUPRAMOLECULAR CHEMISTRY, 1992, 1 (01) :11-14
[5]   GENERAL-METHOD FOR PREPARING ALTROSIDES FROM 2,3-MANNO-EPOXIDES AND ITS APPLICATION TO SYNTHESIS OF ALTERNATIVE BETA-CYCLODEXTRIN WITH AN ALTROSIDE AS THE CONSTITUENT OF MACROCYCLIC STRUCTURE [J].
FUJITA, K ;
OHTA, K ;
IKEGAMI, Y ;
SHIMADA, H ;
TAHARA, T ;
NOGAMI, Y ;
KOGA, T ;
SAITO, K ;
NAKAJIMA, T .
TETRAHEDRON LETTERS, 1994, 35 (51) :9577-9580
[6]  
KAHN AR, 1992, J CHEM SOC CHEM COMM, P1112
[7]   MOLECULAR MODELING OF SACCHARIDES .4. CYCLODEXTRINS, CYCLOMANNINS, AND CYCLOGALACTINS WITH 5 AND 6 (1-]4)-LINKED SUGAR UNITS - A COMPARATIVE-ASSESSMENT OF THEIR CONFORMATIONS AND HYDROPHOBICITY POTENTIAL PROFILES [J].
LICHTENTHALER, FW ;
IMMEL, S .
TETRAHEDRON-ASYMMETRY, 1994, 5 (11) :2045-2060
[8]   STEREOSELECTIVITY OF CYCLOGLYCOSYLATION IN MANNOOLIGOSE SERIES DEPENDS ON CARBOHYDRATE CHAIN-LENGTH - SYNTHESES OF MANNO ISOMERS OF BETA-CYCLODEXTRINS AND GAMMA-CYCLODEXTRINS [J].
MORI, M ;
ITO, Y ;
UZAWA, J ;
OGAWA, T .
TETRAHEDRON LETTERS, 1990, 31 (22) :3191-3194
[9]   A HIGHLY EFFICIENT AND STEREOSELECTIVE CYCLOGLYCOSYLATION - SYNTHESIS OF CYCLO(-]4)-[ALPHA-MAN-(1-]4)]5-ALPHA-MAN-(1-]), A MANNO ISOMER OF ALPHA-CYCLODEXTRIN [J].
MORI, M ;
ITO, Y ;
OGAWA, T .
TETRAHEDRON LETTERS, 1989, 30 (10) :1273-1276
[10]   THE CRYSTAL-STRUCTURE OF CYCLOINULOHEXAOSE PRODUCED FROM INULIN BY CYCLOINULO-OLIGOSACCHARIDE FRUCTANOTRANSFERASE [J].
SAWADA, M ;
TANAKA, T ;
TAKAI, Y ;
HANAFUSA, T ;
TANIGUCHI, T ;
KAWAMURA, M ;
UCHIYAMA, T .
CARBOHYDRATE RESEARCH, 1991, 217 :7-17