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Stereoselective sulfoxidation of α-mannopyranosyl thioglycosides:: The exo-anomeric effect in action
被引:44
作者
:
Crich, D
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Crich, D
Mataka, J
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Mataka, J
Sun, SX
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Sun, SX
Lam, KC
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Lam, KC
Rheingold, AL
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Rheingold, AL
Wink, DJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Wink, DJ
机构
:
[1]
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
[2]
Univ Delaware, Dept Chem & Biochem, Newark, DE 19716 USA
来源
:
CHEMICAL COMMUNICATIONS
|
1998年
/ 24期
关键词
:
D O I
:
10.1039/a804126a
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
As a consequence of the exo-anomeric effect, and in contrast to their beta-anomers, alpha-thioglycosides undergo stereoselective oxidation to give very predominantly the R-sulfoxides, as revealed by X-ray crystallography.
引用
收藏
页码:2763 / 2764
页数:2
相关论文
共 16 条
[1]
Chemistry of 1-alkoxy-1-glycosyl radicals: The manno- and rhamnopyranosyl series. Inversion of alpha- to beta-pyranosides and the fragmentation of anomeric radicals
Crich, D
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, University of Illinois at Chicago, Chicago, IL 60607-7061
Crich, D
Sun, SX
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, University of Illinois at Chicago, Chicago, IL 60607-7061
Sun, SX
Brunckova, J
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, University of Illinois at Chicago, Chicago, IL 60607-7061
Brunckova, J
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1996,
61
(02)
: 605
-
615
[2]
Direct synthesis of β-D-xyl-(1→2)-β-D-man-(1→4)-α-D-Glc-OMe:: a trisaccharide component of the Hyriopsis schlegelii glycosphingolipid
Crich, D
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Crich, D
Dai, ZM
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Dai, ZM
[J].
TETRAHEDRON LETTERS,
1998,
39
(13)
: 1681
-
1684
[3]
Are glycosyl triflates intermediates in the sulfoxide glycosylation method? A chemical and H-1, C-13, and F-19 NMR spectroscopic investigation
Crich, D
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, University of Illinois at Chicago, Chicago, IL 60607-7061
Crich, D
Sun, SX
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, University of Illinois at Chicago, Chicago, IL 60607-7061
Sun, SX
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1997,
119
(46)
: 11217
-
11223
[4]
Direct chemical synthesis of β-mannopyranosides and other glycosides via glycosyl triflates
Crich, D
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Crich, D
Sun, SX
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Sun, SX
[J].
TETRAHEDRON,
1998,
54
(29)
: 8321
-
8348
[5]
Formation of beta-mannopyranosides of primary alcohols using the sulfoxide method
Crich, D
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, University of Illinois at Chicago, Chicago, IL 60607-7061
Crich, D
Sun, SX
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, University of Illinois at Chicago, Chicago, IL 60607-7061
Sun, SX
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1996,
61
(14)
: 4506
-
4507
[6]
Direct synthesis of beta-mannopyranosides by the sulfoxide method
Crich, D
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, University of Illinois at Chicago, Chicago, IL 60607-7061
Crich, D
Sun, SX
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, University of Illinois at Chicago, Chicago, IL 60607-7061
Sun, SX
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1997,
62
(05)
: 1198
-
1199
[7]
Deslongchamps P., 1983, Stereoelectronic Effects in Organic Chemistry
[8]
STEREOCHEMISTRY OF OXIDATION AT SULFUR - OXIDATION OF 4-SUBSTITUTED THIANES TO SULFOXIDES
JOHNSON, CR
论文数:
0
引用数:
0
h-index:
0
JOHNSON, CR
MCCANTS, D
论文数:
0
引用数:
0
h-index:
0
MCCANTS, D
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1965,
87
(05)
: 1109
-
&
[9]
Juaristi E., 1995, ANOMERIC EFFECT, V1st
[10]
GLYCOSYLATION OF UNREACTIVE SUBSTRATES
KAHNE, D
论文数:
0
引用数:
0
h-index:
0
KAHNE, D
WALKER, S
论文数:
0
引用数:
0
h-index:
0
WALKER, S
CHENG, Y
论文数:
0
引用数:
0
h-index:
0
CHENG, Y
VANENGEN, D
论文数:
0
引用数:
0
h-index:
0
VANENGEN, D
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1989,
111
(17)
: 6881
-
6882
←
1
2
→
共 16 条
[1]
Chemistry of 1-alkoxy-1-glycosyl radicals: The manno- and rhamnopyranosyl series. Inversion of alpha- to beta-pyranosides and the fragmentation of anomeric radicals
Crich, D
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, University of Illinois at Chicago, Chicago, IL 60607-7061
Crich, D
Sun, SX
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, University of Illinois at Chicago, Chicago, IL 60607-7061
Sun, SX
Brunckova, J
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, University of Illinois at Chicago, Chicago, IL 60607-7061
Brunckova, J
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1996,
61
(02)
: 605
-
615
[2]
Direct synthesis of β-D-xyl-(1→2)-β-D-man-(1→4)-α-D-Glc-OMe:: a trisaccharide component of the Hyriopsis schlegelii glycosphingolipid
Crich, D
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Crich, D
Dai, ZM
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Dai, ZM
[J].
TETRAHEDRON LETTERS,
1998,
39
(13)
: 1681
-
1684
[3]
Are glycosyl triflates intermediates in the sulfoxide glycosylation method? A chemical and H-1, C-13, and F-19 NMR spectroscopic investigation
Crich, D
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, University of Illinois at Chicago, Chicago, IL 60607-7061
Crich, D
Sun, SX
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, University of Illinois at Chicago, Chicago, IL 60607-7061
Sun, SX
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1997,
119
(46)
: 11217
-
11223
[4]
Direct chemical synthesis of β-mannopyranosides and other glycosides via glycosyl triflates
Crich, D
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Crich, D
Sun, SX
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Sun, SX
[J].
TETRAHEDRON,
1998,
54
(29)
: 8321
-
8348
[5]
Formation of beta-mannopyranosides of primary alcohols using the sulfoxide method
Crich, D
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, University of Illinois at Chicago, Chicago, IL 60607-7061
Crich, D
Sun, SX
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, University of Illinois at Chicago, Chicago, IL 60607-7061
Sun, SX
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1996,
61
(14)
: 4506
-
4507
[6]
Direct synthesis of beta-mannopyranosides by the sulfoxide method
Crich, D
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, University of Illinois at Chicago, Chicago, IL 60607-7061
Crich, D
Sun, SX
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, University of Illinois at Chicago, Chicago, IL 60607-7061
Sun, SX
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1997,
62
(05)
: 1198
-
1199
[7]
Deslongchamps P., 1983, Stereoelectronic Effects in Organic Chemistry
[8]
STEREOCHEMISTRY OF OXIDATION AT SULFUR - OXIDATION OF 4-SUBSTITUTED THIANES TO SULFOXIDES
JOHNSON, CR
论文数:
0
引用数:
0
h-index:
0
JOHNSON, CR
MCCANTS, D
论文数:
0
引用数:
0
h-index:
0
MCCANTS, D
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1965,
87
(05)
: 1109
-
&
[9]
Juaristi E., 1995, ANOMERIC EFFECT, V1st
[10]
GLYCOSYLATION OF UNREACTIVE SUBSTRATES
KAHNE, D
论文数:
0
引用数:
0
h-index:
0
KAHNE, D
WALKER, S
论文数:
0
引用数:
0
h-index:
0
WALKER, S
CHENG, Y
论文数:
0
引用数:
0
h-index:
0
CHENG, Y
VANENGEN, D
论文数:
0
引用数:
0
h-index:
0
VANENGEN, D
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1989,
111
(17)
: 6881
-
6882
←
1
2
→