Sequential ring closing/opening metathesis for the highly selective synthesis of a triply bifunctionalized α-cyclodextrin

被引:32
作者
Bistri, O [1 ]
Sinäy, P [1 ]
Sollogoub, M [1 ]
机构
[1] UPMC, CNRS, ENS,Inst Chim Mol, UMR 8642,Ecole Normale Super,Dept Chim, F-75231 Paris 05, France
关键词
D O I
10.1039/b510329k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Metathesis versatility has been exploited to reveal the cyclic directionality of cyclodextrins and to selectively synthesise a unique cyclodextrin bearing three pairs of orthogonal protecting groups on its primary rim.
引用
收藏
页码:1112 / 1114
页数:3
相关论文
共 23 条
[1]   GEOMETRIC EVIDENCE ON THE RIBONUCLEASE MODEL MECHANISM [J].
ANSLYN, E ;
BRESLOW, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (15) :5972-5973
[2]   Diisobutylaluminium hydride (DIBAL-H) is promoting a selective clockwise debenzylation of perbenzylated 6A 6D-dideoxy-α-cyclodextrin [J].
Bistri, O ;
Sinay, P ;
Sollogoub, M .
TETRAHEDRON LETTERS, 2005, 46 (45) :7757-7760
[3]   Biomimetic reactions catalyzed by cyclodextrins and their derivatives [J].
Breslow, R ;
Dong, SD .
CHEMICAL REVIEWS, 1998, 98 (05) :1997-2011
[4]   BETA-CYCLODEXTRINYLBISIMIDAZOLE, A MODEL FOR RIBONUCLEASE [J].
BRESLOW, R ;
DOHERTY, JB ;
GUILLOT, G ;
LIPSEY, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (10) :3227-3229
[5]   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
[6]   COMPLETE-SETS OF STRUCTURALLY DETERMINED 6A,6X-UNSYMMETRICALLY DISUBSTITUTED BETA-CYCLODEXTRINS - 6A-S-PHENYL-6X-O-(BETA-NAPHTHYLSULFONYL)-6A-THIO-BETA-CYCLODEXTRINS AND 6A-S-(TERT-BUTYL)-6X-O-(BETA-NAPHTHYLSULFONYL)-6A-THIO-BETA-CYCLODEXTRINS [J].
FUJITA, K ;
MATSUNAGA, A ;
YAMAMURA, H ;
IMOTO, T .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (19) :4520-4522
[7]   Preparation of 2A,3A-alloepimino-2A,3A-dideoxy-β-cyclodextrin as a versatile scaffold candidate for the hetero-2A3A-bifunctionalization [J].
Fukudome, M ;
Yuan, DQ ;
Fujita, K .
TETRAHEDRON LETTERS, 2005, 46 (07) :1115-1118
[8]   Recent advances in olefin metathesis and its application in organic synthesis [J].
Grubbs, RH ;
Chang, S .
TETRAHEDRON, 1998, 54 (18) :4413-4450
[9]   Triisobutylaluminium and diisobutylaluminium hydride as molecular scalpels: The regioselective stripping of perbenzylated sugars and cyclodextrins [J].
Lecourt, T ;
Herault, A ;
Pearce, AJ ;
Sollogoub, M ;
Sinay, P .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (12) :2960-2971
[10]   Recent progress in the design and synthesis of artificial enzymes [J].
Motherwell, WB ;
Bingham, MJ ;
Six, Y .
TETRAHEDRON, 2001, 57 (22) :4663-4686