Synthesis of B2,5 type conformationally constrained glucopyranosides

被引:15
作者
Blériot, Y
Vadivel, SK
Greig, IR
Kirby, AJ [1 ]
Sinay, P
机构
[1] Univ Cambridge, Chem Lab, Cambridge CB2 1EW, England
[2] Ecole Normale Super, UMR CNRS 8642, Dept Chim, F-75231 Paris 05, France
关键词
carbohydrates; conformation; hydrolysis;
D O I
10.1016/S0040-4039(03)01631-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Isopropyl and p-nitrophenyl alpha- and beta-D-glucopyranosides restrained in a conformation close to B-2,B-5 have been synthesized. They are all hydrolyzed at similar rates, close to those observed for the parent unlocked glucosides. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6687 / 6690
页数:4
相关论文
共 29 条
[1]   Facile cleavage of carbohydrate benzyl ethers and benzylidene acetals using the NaBrO3/Na2S2O4 reagent under two-phase conditions [J].
Adinolfi, M ;
Barone, G ;
Guariniello, L ;
Iadonisi, A .
TETRAHEDRON LETTERS, 1999, 40 (48) :8439-8441
[2]   Theoretical modelling of kinetic isotope effects for glycoside hydrolysis in aqueous solution by a hybrid quantum-mechanical molecular-mechanical method [J].
Barnes, JA ;
Williams, IH .
CHEMICAL COMMUNICATIONS, 1996, (02) :193-194
[3]   COMPLETE KINETIC ISOTOPE EFFECT DESCRIPTION OF TRANSITION-STATES FOR ACID-CATALYZED HYDROLYZES OF METHYL ALPHA-GLUCOPYRANOSIDES AND BETA-GLUCOPYRANOSIDES [J].
BENNET, AJ ;
SINNOTT, ML .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (23) :7287-7294
[4]   MECHANISM IN CARBOHYDRATE CHEMISTRY [J].
CAPON, B .
CHEMICAL REVIEWS, 1969, 69 (04) :407-+
[5]  
Das S. K., 2001, ANGEW CHEM, V113, P1723
[6]  
Das SK, 2001, CHEM-EUR J, V7, P4821
[7]  
Das SK, 2001, ANGEW CHEM INT EDIT, V40, P1670, DOI 10.1002/1521-3773(20010504)40:9<1670::AID-ANIE16700>3.3.CO
[8]  
2-H
[9]  
DAVIES G, 1997, COMPREHENSIVE BIOL C, V1, P119
[10]   Stereoelectronic effects on reactivity. Crystal-structure-reactivity correlations for acetals with synperiplanar lone pairs [J].
Deslongchamps, P ;
Jones, PG ;
Li, S ;
Kirby, AJ ;
Kuusela, S ;
Ma, Y .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1997, (12) :2621-2626