A very efficient synthesis of a mannosyl orthoester [2]rotaxane and mannosidic [2]rotaxanes

被引:30
作者
Coutrot, Frederic [1 ]
Busseron, Eric
Montero, Jean-Louis
机构
[1] Univ Montpellier 2, UMR CNRS 5247, IBMM, Ecole Natl Super Chim Montpellier, F-34296 Montpellier 5, France
关键词
D O I
10.1021/ol702779z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The direct preparation of mannosyl[2]rotaxane derivatives by O-glycosylation from tetra-O-acetyl-alpha-D-mannosyltrichloroacetimidate and a tert-butylanilinium alcohol in the presence of dibenzo-24-crown-8 is described. The method appears to be very efficient and allows for the preparation of either orthoester or mannosyl rotaxane derivatives, depending on reaction conditions.
引用
收藏
页码:753 / 756
页数:4
相关论文
共 32 条
[1]  
AECHUT A, 1997, LIEBIGS ANN-RECL, P495
[2]   Interlocked and intertwined structures and superstructures [J].
Amabilino, DB ;
Stoddart, JF .
CHEMICAL REVIEWS, 1995, 95 (08) :2725-2828
[3]   DIALKYLAMMONIUM ION CROWN-ETHER COMPLEXES - THE FORERUNNERS OF A NEW FAMILY OF INTERLOCKED MOLECULES [J].
ASHTON, PR ;
CAMPBELL, PJ ;
CHRYSTAL, EJT ;
GLINK, PT ;
MENZER, S ;
PHILP, D ;
SPENCER, N ;
STODDART, JF ;
TASKER, PA ;
WILLIAMS, DJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (17) :1865-1869
[4]   Self-assembly of a water-soluble [2]rotaxane with carbohydrate stoppers [J].
Ashton, PR ;
Everitt, SRL ;
GomezLopez, M ;
Jayaraman, N ;
Stoddart, JF .
TETRAHEDRON LETTERS, 1997, 38 (32) :5691-5694
[5]  
Balzani V, 2000, ANGEW CHEM INT EDIT, V39, P3348, DOI 10.1002/1521-3773(20001002)39:19<3348::AID-ANIE3348>3.0.CO
[6]  
2-X
[7]   Determining the intracellular transport mechanism of a cleft-[2]rotaxane [J].
Bao, Xiaofeng ;
Isaacsohn, Idit ;
Drew, Angela F. ;
Smithrud, David B. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (37) :12229-12238
[8]   Monitoring cyclodextrin-polyviologen pseudopolyrotaxanes with the Bradford assay [J].
Belitsky, JM ;
Nelson, A ;
Stoddart, JF .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (02) :250-256
[9]   Pseudorotaxanes and rotaxanes formed by viologen derivatives [J].
Braunschweig, AB ;
Ronconi, CM ;
Han, JY ;
Aricó, F ;
Cantrill, SJ ;
Stoddart, JF ;
Khan, SI ;
White, AJP ;
Williams, DJ .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (08) :1857-1866
[10]   Host-[2] rotaxanes as cellular transport agents [J].
Dvornikovs, V ;
House, BE ;
Kaetzel, M ;
Dedman, JR ;
Smithrud, DB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (27) :8290-8301