Palladium-catalyzed oxidation of benzylated aldose hemiacetals to lactones

被引:16
作者
Bessmertnykh, A [1 ]
Hénin, F [1 ]
Muzart, J [1 ]
机构
[1] Univ Reims, CNRS, Unite Mixte Rech React Select & Applicat, F-51687 Reims, France
关键词
oxidation; catalysis; palladium; sugar hemiacetals; sugar lactones; bromobenzene;
D O I
10.1016/j.carres.2004.02.014
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Benzyl protected sugar hemiacetals are oxidized to the corresponding lactones in excellent yields using bromobenzene, K2CO3 and the Pd(OAc)(2)/PPh3 catalytic system. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1377 / 1380
页数:4
相关论文
共 26 条
[1]  
Arts SJHF, 1997, SYNTHESIS-STUTTGART, P597
[2]   Selective oxidation of alcohols and aldehydes on metal catalysts [J].
Besson, M ;
Gallezot, P .
CATALYSIS TODAY, 2000, 57 (1-2) :127-141
[3]   Sulfonic acid analogues of the sialyl Lewis X tetrasaccharide [J].
Borbás, A ;
Szabovik, G ;
Antal, Z ;
Fehér, K ;
Csávás, M ;
Szilágyi, L ;
Herczegh, P ;
Lipták, A .
TETRAHEDRON-ASYMMETRY, 2000, 11 (02) :549-566
[4]   MONTMORILLONITE SUBSTRATE SELECTIVITY IN ALCOHOL OXIDATION [J].
CHOUDARY, BM ;
RANI, SS ;
RAO, YVS ;
KANTAM, ML .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (09) :2274-2275
[5]   PALLADIUM CATALYZED OXIDATION OF PRIMARY AND SECONDARY ALCOHOLS UNDER SOLID-LIQUID PHASE-TRANSFER CONDITIONS [J].
CHOUDARY, BM ;
REDDY, NP ;
KANTAM, ML ;
JAMIL, Z .
TETRAHEDRON LETTERS, 1985, 26 (50) :6257-6258
[6]   Easy access to C-glycosides from aldonolactones by a claisen-type chain-extension reaction [J].
Csuk, R ;
Kuhn, M ;
Strohl, D .
TETRAHEDRON, 1997, 53 (04) :1311-1322
[7]  
deNooy AEJ, 1996, SYNTHESIS-STUTTGART, P1153
[8]   Selective oxidation with air on metal catalysts [J].
Gallezot, P .
CATALYSIS TODAY, 1997, 37 (04) :405-418
[9]   REACTION OF PYRANOID AND FURANOID ALDONOLACTONES WITH CHLOROMETHYLTRIMETHYLSILANE-DERIVED REAGENTS [J].
GLANZER, BI ;
CSUK, R .
CARBOHYDRATE RESEARCH, 1991, 220 :79-92
[10]   A facile synthesis of per-O-alkylated glycono-delta-lactones from per-O-alkylated glycopyranosides and a novel ring contraction for pyranoses [J].
Goebel, M ;
Nothofer, HG ;
Ross, G ;
Ugi, I .
TETRAHEDRON, 1997, 53 (09) :3123-3134