Ph2SO/Tf2O:: a powerful promotor system in chemoselective glycosylations using thioglycosides

被引：206

作者：

Codée, JDC ^{[1
]}

Litjens, REJN ^{[1
]}

den Heeten, R ^{[1
]}

Overkleeft, HS ^{[1
]}

van Boom, JH ^{[1
]}

van der Marel, GA ^{[1
]}

机构：

[1] Leiden Univ, Leiden Inst Chem, NL-2300 RA Leiden, Netherlands

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 09期

关键词：

D O I：

10.1021/ol034312t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Diphenylsulfoxide in combination with triflic anhydride provides a very potent thiophilic glycosylation promotor system, capable of activating disarmed thioglycosides. The usefulness of this novel thiophilic activator is illustrated in a successful chemoselective glycosylation sequence in which the donor thioglycoside in the first condensation step may be either armed or disarmed.

引用

页码：1519 / 1522

页数：4

共 45 条

[1] Rapid assembly of oligosaccharides: 1,2-diacetal-mediated reactivity tuning in the coupling of glycosyl fluorides [J].

Baeschlin, DK ;

Green, LG ;

Hahn, MG ;

Hinzen, B ;

Ince, SJ ;

Ley, SV .

TETRAHEDRON-ASYMMETRY, 2000, 11 (01) :173-197

[2] CHEMOSELECTIVE GLYCOSYLATIONS .1. DIFFERENCES IN SIZE OF ANOMERIC LEAVING GROUPS CAN BE EXPLOITED IN CHEMOSELECTIVE GLYCOSYLATIONS [J].

BOONS, GJ ;

GEURTSEN, R ;

HOLMES, D .

TETRAHEDRON LETTERS, 1995, 36 (35) :6325-6328

[3] Strategies in oligosaccharide synthesis [J].

Boons, GJ .

TETRAHEDRON, 1996, 52 (04) :1095-1121

[4]

Burkhart F, 2001, ANGEW CHEM INT EDIT, V40, P1274, DOI 10.1002/1521-3773(20010401)40:7<1274::AID-ANIE1274>3.0.CO

[5]

2-W

[6]

Codée JDC, 2002, EUR J ORG CHEM, V2002, P3954, DOI 10.1002/1099-0690(200212)2002:23<3954::AID-EJOC3954>3.0.CO

[7]

2-2

[8] Solid-phase synthesis of β-mannosides [J].

Crich, D ;

Smith, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (30) :8867-8869

[9] Synthesis of the salmonella type E1 core trisaccharide as a probe for the generality of 1-(benzenesulfinyl)piperidine/triflic anhydride combination for glycosidic bond formation from thioglycosides [J].

Crich, D ;

Li, HM .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14) :4640-4646

[10] S-(4-Methoxyphenyl) benzenethiosulfinate (MPBT) trifluoromethanesulfonic anhydride:: A convenient system for the generation of glycosyl triflates from thioglycosides [J].

Crich, D ;

Smith, M .

ORGANIC LETTERS, 2000, 2 (25) :4067-4069

← 1 2 3 4 5 →