The S-xanthenyl group:: potential for application in the synthesis of thioglycosides

被引:11
作者
Falconer, RA [1 ]
机构
[1] Univ London, Sch Pharm, Dept Pharmaceut & Biol Chem, London WC1N 1AX, England
关键词
D O I
10.1016/S0040-4039(02)02070-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The S-xanthenyl (Xan) group was demonstrated to have potential as a convenient protecting group for 1-thiosugars in the synthesis of thioglycosides. Easily introduced by reaction of a 1-thiosugar with 9-hydroxyxanthene in the presence of catalytic TFA, the S-Xan group is compatible with a wide range of functionalities and protecting groups. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8503 / 8505
页数:3
相关论文
共 20 条
[1]   p-toluenesulfonylacetylene as thiol protecting group [J].
Arjona, O ;
Iradier, F ;
Medel, R ;
Plumet, J .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (16) :6090-6093
[2]  
Barlos K, 1996, INT J PEPT PROT RES, V47, P148
[3]  
Bertozzi C. R., 1996, MODERN METHODS CARBO, P316
[4]  
BODANSZKY M, 1982, INT J PEPT PROT RES, V20, P434
[5]   ON THE USE OF S-TERT-BUTYLSULPHENYL GROUP FOR PROTECTION OF CYSTEINE IN SOLID-PHASE PEPTIDE-SYNTHESIS USING FMOC-AMINO ACIDS [J].
ERITJA, R ;
ZIEHLERMARTIN, JP ;
WALKER, PA ;
LEE, TD ;
LEGESSE, K ;
ALBERICIO, F ;
KAPLAN, BE .
TETRAHEDRON, 1987, 43 (12) :2675-2680
[6]  
Garegg PJ, 1997, ADV CARBOHYD CHEM BI, V52, P179, DOI 10.1016/S0065-2318(08)60091-8
[7]   Allylic protection of thiols and cysteine.: III.: Use of Fmoc-Cys(Fsam)-OH for solid-phase peptide synthesis [J].
Gomez-Martinez, P ;
Guibé, F ;
Albericio, F .
LETTERS IN PEPTIDE SCIENCE, 2000, 7 (04) :187-194
[8]  
Greene T. W., 1999, PROTECTIVE GROUPS OR, P454, DOI 10.1002/0471220574.ch6
[9]   Controlled syntheses of natural and disulfide-mispaired regioisomers of α-conotoxin SI [J].
Hargittai, B ;
Barany, G .
JOURNAL OF PEPTIDE RESEARCH, 1999, 54 (06) :468-479
[10]  
HIN Y, 1997, J ORG CHEM, V62, P3841