Synthesis of phenyl 1-thioglycopyranosiduronic acids using a sonicated Jones oxidation

被引:14
作者
Allanson, NM [1 ]
Liu, DS [1 ]
Chi, F [1 ]
Jain, RK [1 ]
Chen, A [1 ]
Ghosh, M [1 ]
Hong, LW [1 ]
Sofia, MJ [1 ]
机构
[1] Transcell Technol Inc, Cranbury, NJ 08512 USA
关键词
D O I
10.1016/S0040-4039(98)00155-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Jones reagent selectively oxidizes the primary hydroxyl of 1-thiophenyl glycosides in preference to oxidation at sulfur to give phenyl 1-thioglycopyranosiduronic acids in moderate to excellent yields. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1889 / 1892
页数:4
相关论文
共 9 条
[1]   SELECTIVE OXIDATION OF MONOSACCHARIDE DERIVATIVES TO URONIC-ACIDS [J].
DAVIS, NJ ;
FLITSCH, SL .
TETRAHEDRON LETTERS, 1993, 34 (07) :1181-1184
[2]   MOENOMYCIN-A - A STRUCTURAL REVISION AND NEW STRUCTURE-ACTIVITY RELATIONS [J].
FEHLHABER, HW ;
GIRG, M ;
SEIBERT, G ;
HOBERT, K ;
WELZEL, P ;
VANHEIJENOORT, Y ;
VANHEIJENOORT, J .
TETRAHEDRON, 1990, 46 (05) :1557-1568
[3]   SYNTHESIS OF 4-O-(ALPHA-L-RHAMNOPYRANOSYL)-D-GLUCOPYRANURONIC ACID [J].
FUGEDI, P .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1987, 6 (03) :377-398
[4]  
HAINES AJ, 1976, ADV CARBOHYD CHEM, V4, P11
[5]  
HEYNS K, 1962, ADV CARBOHYD CHEM, V17, P169
[6]   An efficient and highly stereoselective alpha(1->4) glycosylation between two D-galacturonic acid ester derivatives [J].
Magaud, D ;
Grandjean, C ;
Doutheau, A ;
Anker, D ;
Shevchik, V ;
CottePattat, N ;
RobertBaudouy, J .
TETRAHEDRON LETTERS, 1997, 38 (02) :241-244
[7]  
MEINWALD J, ORGANIC SYNTHESES, V5, P866
[8]  
NAKAHARA Y, 1988, CARBOHYD RES, V175, P306
[9]   D-GALACTOSE-DERIVED D-GALACTURONIC ACID-DERIVATIVES SUITABLE AS GLYCOSYL ACCEPTORS [J].
STEFFAN, W ;
VOGEL, C ;
KRISTEN, H .
CARBOHYDRATE RESEARCH, 1990, 204 :109-120