Sequential one-pot glycosylations using 1-hydroxyl and 1-thiodonors

被引：85

作者：

Codée, JDC ^{[1
]}

van den Bos, LJ ^{[1
]}

Litjens, REJN ^{[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 / 11期

关键词：

D O I：

10.1021/ol034528v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHIC] A novel sequential glycosylation procedure is described that combines the use of 1-hydroxyl and thiodonors. The Ph2SO/Tf2O-mediated dehydrative condensation of 1-hydroxyl donors with thioglycosides affords in good yield the thiodisaccharides, which in turn can be activated by the same activator system to furnish trisaccharides. The alpha-Gal epitope and a hyaluronan trisaccharide were efficiently assembled in a one-pot procedure.

引用

页码：1947 / 1950

页数：4

共 57 条

[1] Rapid assembly of oligosaccharides: 1,2-diacetal-mediated reactivity tuning in the coupling of glycosyl fluorides
Baeschlin, DK
Green, LG
Hahn, MG
Hinzen, B
Ince, SJ
Ley, SV
[J]. TETRAHEDRON-ASYMMETRY, 2000, 11 (01) : 173 - 197
[2] Strategies in oligosaccharide synthesis
Boons, GJ
[J]. TETRAHEDRON, 1996, 52 (04) : 1095 - 1121
[3] Burkhart F, 2001, ANGEW CHEM INT EDIT, V40, P1274, DOI 10.1002/1521-3773(20010401)40:7<1274::AID-ANIE1274>3.0.CO
[4] 2-W
[5] Ph2SO/Tf2O:: a powerful promotor system in chemoselective glycosylations using thioglycosides
Codée, JDC
Litjens, REJN
den Heeten, R
Overkleeft, HS
van Boom, JH
van der Marel, GA
[J]. ORGANIC LETTERS, 2003, 5 (09) : 1519 - 1522
[6] Cooper D K, 1993, Transpl Immunol, V1, P198, DOI 10.1016/0966-3274(93)90047-C
[7] COOPER DKC, 1992, CLIN TRANSPLANT, V6, P178
[8] 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
Crich, D
Li, HM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14) : 4640 - 4646
[9] S-(4-Methoxyphenyl) benzenethiosulfinate (MPBT) trifluoromethanesulfonic anhydride:: A convenient system for the generation of glycosyl triflates from thioglycosides
Crich, D
Smith, M
[J]. ORGANIC LETTERS, 2000, 2 (25) : 4067 - 4069
[10] 1-Benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride: A potent combination of shelf-stable reagents for the low-temperature conversion of thioglycosides to glycosyl triflates and for the formation of diverse glycosidic linkages
Crich, D
Smith, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (37) : 9015 - 9020

← 1 2 3 4 5 6 →