2-Nitro thioglycoside donors:: Versatile precursors of β-D-glycosides of aminosugars

被引：32

作者：

Barroca, N ^{[1
]}

Schmidt, RR ^{[1
]}

机构：

[1] Univ Konstanz, Dept Chem, D-78457 Constance, Germany

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 10期

关键词：

D O I：

10.1021/ol049729t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Nitro thioglycosides can be prepared by the Michael addition of thiophenol to 2-nitroglycal derivatives. NIS/TMSOTf activation of these 2-nitro thioglycosides, in the presence of alcohols, rapidly and cleanly led to the desired glycosides in good yield and beta-selectivity. Reduction of the nitro group allowed generation of the corresponding 2-acetamido glycosides.

引用

页码：1551 / 1554

页数：4

共 27 条

[1] CIRCULAR-DICHROISM OF ACETYLATED METHYL GLYCOSIDES .2.
BOREN, HB
GAREGG, PJ
KENNE, L
PILOTTI, A
SVENSSON, S
SWAHN, CG
[J]. ACTA CHEMICA SCANDINAVICA, 1973, 27 (08): : 2740 - 2748
[2] Synthesis of tumor-associated glycopeptide antigens
Brocke, C
Kunz, H
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (10) : 3085 - 3112
[3] Pathways of O-glycan biosynthesis in cancer cells
Brockhausen, I
[J]. BIOCHIMICA ET BIOPHYSICA ACTA-GENERAL SUBJECTS, 1999, 1473 (01): : 67 - 95
[4] 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
[5] 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
[6] Chemistry of 4,6-O-benzylidene-D-glycopyranosyl triflates:: Contrasting behavior between the gluco and manno series
Crich, D
Cai, WL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (13) : 4926 - 4930
[7] Formation of beta-mannopyranosides of primary alcohols using the sulfoxide method
Crich, D
Sun, SX
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (14) : 4506 - 4507
[8] Das J, 1998, EUR J ORG CHEM, V1998, P1609
[9] GEIGER J, 2004, IN PRESS SYNLETT
[10] 2-NITROGLYCALS - PREPARATION AND NUCLEOPHILIC-ADDITION REACTIONS
HOLZAPFEL, CW
MARAIS, CF
VANDYK, MS
[J]. SYNTHETIC COMMUNICATIONS, 1988, 18 (01) : 97 - 114

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