Iminosugar thioglycosides as glycosyl donors: a route to disaccharides with an iminosugar moiety

被引：4

作者：

Fuentes, Jose ^{[1
,2
]}

Al Bujuq, Nader R. ^{[1
,2
]}

Angulo, Manuel ^{[1
,2
]}

Gasch, Consolacion ^{[1
,2
]}

机构：

[1] Univ Seville, Dept Quim Organ, E-41071 Seville, Spain

[2] Univ Seville, Serv RMN, E-41071 Seville, Spain

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 05期

关键词：

immosugars; thioglycosides; glycosidations; iminosugar-disaccharides;

D O I：

10.1016/j.tetlet.2007.11.160

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The immosugar thioglycosides are used as glycosyl donors in glycosidation reactions. Thereby, iminosugar glycosides and disaccharide analogues with an iminosugar moiety are prepared. The yields are high and the method is stereoselective. (C) 2007 Elsevier Ltd. All rights reserved.

引用

页码：910 / 913

页数：4

共 39 条

[1] Recent advances in the chemistry of azapyranose sugars
Afarinkia, K
Bahar, A
[J]. TETRAHEDRON-ASYMMETRY, 2005, 16 (07) : 1239 - 1287
[2] AGRYROPOULOS N, 2004, TETRAHEDRON LETT, V45, P4237
[3] Synthesis of C-disaccharide analogues of the α-D-arabinofuranosyl-(1→5)-α-D-arabinofuranosyl motif of mycobacterial cell walls via alkynyl intermediates
Aslam, T
Fuchs, MGG
Le Formal, A
Wightman, RH
[J]. TETRAHEDRON LETTERS, 2005, 46 (18) : 3249 - 3252
[4] SYNTHESIS OF THE FIRST PSEUDOSUGAR-C-DISACCHARIDE - A POTENTIAL ANTIGEN FOR ELICITING GLYCOSIDE-BOND FORMING ANTIBODIES WITH CATALYTIC GROUPS
BARBAUD, C
BOLS, M
LUNDT, I
SIERKS, MR
[J]. TETRAHEDRON, 1995, 51 (33) : 9063 - 9078
[5] SYNTHESIS OF (+)-1,5-DIDEOXY-1,5-IMINO-D-GALACTITOL, A POTENT ALPHA-D-GALACTOSIDASE INHIBITOR
BERNOTAS, RC
PEZZONE, MA
GANEM, B
[J]. CARBOHYDRATE RESEARCH, 1987, 167 : 305 - 311
[6] C-3- and C-4-alkylated polyhydroxypyrrolidines: Enantiospecific syntheses and glycosidase inhibitory activity
Blanco, MJ
Sardina, FJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10) : 3411 - 3416
[7] One step synthesis of sulfur and nitrogen linked aza-disaccharide precursors from D-mannitol derived bis-aziridines
Campanini, L
Dureault, A
Depezay, JC
[J]. TETRAHEDRON LETTERS, 1996, 37 (29) : 5095 - 5098
[8] STEREOSELECTIVE APPROACHES TO BIOACTIVE CARBOHYDRATES AND ALKALOIDS - WITH A FOCUS ON RECENT SYNTHESES DRAWING FROM THE CHIRAL POOL
CASIRAGHI, G
ZANARDI, F
RASSU, G
SPANU, P
[J]. CHEMICAL REVIEWS, 1995, 95 (06) : 1677 - 1716
[9] Total synthesis of hyacinthacine A1 and 3-epi-hyacinthacine A1
Chabaud, L
Landais, Y
Renaud, P
[J]. ORGANIC LETTERS, 2005, 7 (13) : 2587 - 2590
[10] Direct formation of β-mannopyranosides and other hindered glycosides from thioglycosides
Crich, D
Sun, SX
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (02) : 435 - 436

← 1 2 3 4 →