Trifluoroethylsulfonate protected monosaccharides in glycosylation reactions

被引：19
作者：
Karst, NA
Islam, TF
Avci, FY
Linhardt, RJ [1 ]
机构：
[1] Rensselaer Polytech Inst, Dept Chem & Chem Biol, Troy, NY 12180 USA
[2] Rensselaer Polytech Inst, Dept Biol, Troy, NY 12180 USA
[3] Rensselaer Polytech Inst, Dept Chem & Biol Engn, Troy, NY 12180 USA
[4] Univ Iowa, Dept Chem, Iowa City, IA 52242 USA
来源：
TETRAHEDRON LETTERS | 2004年 / 45卷 / 34期
关键词：
trifluoroethylsulfonate; glycosylation; glycosaminoglycans;
D O I：
10.1016/j.tetlet.2004.06.131
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A variety of sulfo-protected monosaccharide donors and acceptors were investigated in glycosylation reactions. Trifluoro-ethylsulfonate (SO3TFE) group was compatible with a wide range of activation conditions commonly used with fluoride, imidate, and sulfide donors. In addition, the influence of a SO3TFE group, at the critical 2-position in glycosyl donor, on the stereoselectivity of the glycosylation reaction was studied. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6433 / 6437
页数：5
相关论文
共 18 条
[1]   Synthetic oligosaccharides as heparin-mimetics displaying anticoagulant properties [J].
Avci, FY ;
Karst, NA ;
Linhardt, RJ .
CURRENT PHARMACEUTICAL DESIGN, 2003, 9 (28) :2323-2335
[2]   Ph2SO/Tf2O:: a powerful promotor system in chemoselective glycosylations using thioglycosides [J].
Codée, JDC ;
Litjens, REJN ;
den Heeten, R ;
Overkleeft, HS ;
van Boom, JH ;
van der Marel, GA .
ORGANIC LETTERS, 2003, 5 (09) :1519-1522
[3]   Scavenging byproducts in the sulfoxide glycosylation reaction: Application to the synthesis of ciclamycin 0 [J].
Gildersleeve, J ;
Smith, A ;
Sakurai, K ;
Raghavan, S ;
Kahne, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (26) :6176-6182
[4]   Rapid synthesis of a glycosylphosphatidylinositol-based malaria vaccine using automated solid-phase oligosaccharide synthesis [J].
Hewitt, MC ;
Snyder, DA ;
Seeberger, PH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (45) :13434-13436
[5]  
Islam T., 2003, CARBOHYRATE BASEDDRU, V1, P407
[6]   Borane/Bu2BOTf:: A mild reagent for the regioselective reductive ring opening of benzylidene acetals in carbohydrates [J].
Jiang, L ;
Chan, TH .
TETRAHEDRON LETTERS, 1998, 39 (5-6) :355-358
[7]  
Karst N, 2002, EUR J ORG CHEM, V2002, P815, DOI 10.1002/1099-0690(200203)2002:5<815::AID-EJOC815>3.0.CO
[8]  
2-A
[9]   Chemical synthesis of β-D-GlcpA(2SO4)-(1→3)-D-GalpNAc(6SO4), the disaccharide repeating unit of shark cartilage chondroitin sulfate D, and of its methyl β-D-glycoside derivative [J].
Karst, N ;
Jacquinet, JC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (16) :2709-2717
[10]   Recent chemical and enzymatic approaches to the synthesis of glycosaminoglycan oligosaccharides [J].
Karst, NA ;
Linhardt, RJ .
CURRENT MEDICINAL CHEMISTRY, 2003, 10 (19) :1993-2031
12