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A direct organocatalytic entry to sphingoids:: asymmetric synthesis of D-arabino- and L-ribo-phytosphingosine
被引:82
作者
:
Enders, D
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Enders, D
[
1
]
Palecek, J
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Palecek, J
[
1
]
Grondal, C
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Grondal, C
[
1
]
机构
:
[1]
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
来源
:
CHEMICAL COMMUNICATIONS
|
2006年
/ 06期
关键词
:
D O I
:
10.1039/b515007h
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
The organocatalytic asymmetric synthesis of D-arabino- and L-ribo-phytosphingosine is described employing a diastereo-and enantioselective (S)-proline-catalyzed aldol reaction of 2,2-dimethyl-1,3-dioxan-5-one and pentadecanal as the key step.
引用
收藏
页码:655 / 657
页数:3
相关论文
共 56 条
[1]
UTILIZATION AND DEGRADATION OF PHYTOSPHINGOSINE BY RAT LIVER
BARENHOLZ, Y
论文数:
0
引用数:
0
h-index:
0
BARENHOLZ, Y
GATT, S
论文数:
0
引用数:
0
h-index:
0
GATT, S
[J].
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS,
1967,
27
(03)
: 319
-
+
[2]
Bioorganic chemistry of ceramide
Brodesser, S
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany
Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany
Brodesser, S
Sawatzki, P
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany
Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany
Sawatzki, P
Kolter, T
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany
Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany
Kolter, T
[J].
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,
2003,
2003
(11)
: 2021
-
2034
[3]
CARTER HE, 1954, J BIOL CHEM, V206, P613
[4]
A facile synthesis of phytosphingosine from diisopropylidene-D-mannofuranose
Chiu, HY
论文数:
0
引用数:
0
h-index:
0
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Acad Sinica, Inst Chem, Taipei 115, Taiwan
Acad Sinica, Inst Chem, Taipei 115, Taiwan
Chiu, HY
Tzou, DLM
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0
引用数:
0
h-index:
0
机构:
Acad Sinica, Inst Chem, Taipei 115, Taiwan
Acad Sinica, Inst Chem, Taipei 115, Taiwan
Tzou, DLM
Patkar, LN
论文数:
0
引用数:
0
h-index:
0
机构:
Acad Sinica, Inst Chem, Taipei 115, Taiwan
Acad Sinica, Inst Chem, Taipei 115, Taiwan
Patkar, LN
Lin, CC
论文数:
0
引用数:
0
h-index:
0
机构:
Acad Sinica, Inst Chem, Taipei 115, Taiwan
Acad Sinica, Inst Chem, Taipei 115, Taiwan
Lin, CC
[J].
JOURNAL OF ORGANIC CHEMISTRY,
2003,
68
(14)
: 5788
-
5791
[5]
Synthesis of a ceramide sphingolipid as a potential sex pheromone of the hair crab Erimacrus isenbeckii using butane-2,3-diacetal desymmetrised glycolic acid building blocks
Dixon, DJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Dixon, DJ
Ley, SV
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Ley, SV
Lohmann, S
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Lohmann, S
Sheppard, TD
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Sheppard, TD
[J].
SYNLETT,
2005,
(03)
: 481
-
484
[6]
DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF L-THREO-SPHINGOSINE AND D-ERYTHRO-SPHINGOSINE
ENDERS, D
论文数:
0
引用数:
0
h-index:
0
机构:
Institut Für Organische Chemie, Technischen Hochschule, Aachen, D-52074
ENDERS, D
WHITEHOUSE, DL
论文数:
0
引用数:
0
h-index:
0
机构:
Institut Für Organische Chemie, Technischen Hochschule, Aachen, D-52074
WHITEHOUSE, DL
RUNSINK, J
论文数:
0
引用数:
0
h-index:
0
机构:
Institut Für Organische Chemie, Technischen Hochschule, Aachen, D-52074
RUNSINK, J
[J].
CHEMISTRY-A EUROPEAN JOURNAL,
1995,
1
(06)
: 382
-
388
[7]
Asymmetric synthesis of selectively protected amino sugars and derivatives by a direct organocatalytic Mannich reaction
Enders, D
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Enders, D
Grondal, C
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Grondal, C
Vrettou, M
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Vrettou, M
Raabe, G
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Raabe, G
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2005,
44
(26)
: 4079
-
4083
[8]
Direct organocatalytic de novo synthesis of carbohydrates
Enders, D
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH Aachen Klinikum, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH Aachen Klinikum, Inst Organ Chem, D-52074 Aachen, Germany
Enders, D
Grondal, C
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH Aachen Klinikum, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH Aachen Klinikum, Inst Organ Chem, D-52074 Aachen, Germany
Grondal, C
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2005,
44
(08)
: 1210
-
1212
[9]
The dihydroxyacetone unit -: A versatile C3 building block in organic synthesis
Enders, D
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Enders, D
Voith, M
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Voith, M
Lenzen, A
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Lenzen, A
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2005,
44
(09)
: 1304
-
1325
[10]
Asymmetric synthesis of 2-amino-1,3-diols and D-erythro-sphinganine
Enders, D
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Enders, D
Müller-Hüwen, A
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Müller-Hüwen, A
[J].
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,
2004,
2004
(08)
: 1732
-
1739
←
1
2
3
4
5
6
→
共 56 条
[1]
UTILIZATION AND DEGRADATION OF PHYTOSPHINGOSINE BY RAT LIVER
BARENHOLZ, Y
论文数:
0
引用数:
0
h-index:
0
BARENHOLZ, Y
GATT, S
论文数:
0
引用数:
0
h-index:
0
GATT, S
[J].
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS,
1967,
27
(03)
: 319
-
+
[2]
Bioorganic chemistry of ceramide
Brodesser, S
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany
Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany
Brodesser, S
Sawatzki, P
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany
Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany
Sawatzki, P
Kolter, T
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany
Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany
Kolter, T
[J].
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,
2003,
2003
(11)
: 2021
-
2034
[3]
CARTER HE, 1954, J BIOL CHEM, V206, P613
[4]
A facile synthesis of phytosphingosine from diisopropylidene-D-mannofuranose
Chiu, HY
论文数:
0
引用数:
0
h-index:
0
机构:
Acad Sinica, Inst Chem, Taipei 115, Taiwan
Acad Sinica, Inst Chem, Taipei 115, Taiwan
Chiu, HY
Tzou, DLM
论文数:
0
引用数:
0
h-index:
0
机构:
Acad Sinica, Inst Chem, Taipei 115, Taiwan
Acad Sinica, Inst Chem, Taipei 115, Taiwan
Tzou, DLM
Patkar, LN
论文数:
0
引用数:
0
h-index:
0
机构:
Acad Sinica, Inst Chem, Taipei 115, Taiwan
Acad Sinica, Inst Chem, Taipei 115, Taiwan
Patkar, LN
Lin, CC
论文数:
0
引用数:
0
h-index:
0
机构:
Acad Sinica, Inst Chem, Taipei 115, Taiwan
Acad Sinica, Inst Chem, Taipei 115, Taiwan
Lin, CC
[J].
JOURNAL OF ORGANIC CHEMISTRY,
2003,
68
(14)
: 5788
-
5791
[5]
Synthesis of a ceramide sphingolipid as a potential sex pheromone of the hair crab Erimacrus isenbeckii using butane-2,3-diacetal desymmetrised glycolic acid building blocks
Dixon, DJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Dixon, DJ
Ley, SV
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Ley, SV
Lohmann, S
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Lohmann, S
Sheppard, TD
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Sheppard, TD
[J].
SYNLETT,
2005,
(03)
: 481
-
484
[6]
DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF L-THREO-SPHINGOSINE AND D-ERYTHRO-SPHINGOSINE
ENDERS, D
论文数:
0
引用数:
0
h-index:
0
机构:
Institut Für Organische Chemie, Technischen Hochschule, Aachen, D-52074
ENDERS, D
WHITEHOUSE, DL
论文数:
0
引用数:
0
h-index:
0
机构:
Institut Für Organische Chemie, Technischen Hochschule, Aachen, D-52074
WHITEHOUSE, DL
RUNSINK, J
论文数:
0
引用数:
0
h-index:
0
机构:
Institut Für Organische Chemie, Technischen Hochschule, Aachen, D-52074
RUNSINK, J
[J].
CHEMISTRY-A EUROPEAN JOURNAL,
1995,
1
(06)
: 382
-
388
[7]
Asymmetric synthesis of selectively protected amino sugars and derivatives by a direct organocatalytic Mannich reaction
Enders, D
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Enders, D
Grondal, C
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Grondal, C
Vrettou, M
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Vrettou, M
Raabe, G
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Raabe, G
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2005,
44
(26)
: 4079
-
4083
[8]
Direct organocatalytic de novo synthesis of carbohydrates
Enders, D
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH Aachen Klinikum, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH Aachen Klinikum, Inst Organ Chem, D-52074 Aachen, Germany
Enders, D
Grondal, C
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH Aachen Klinikum, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH Aachen Klinikum, Inst Organ Chem, D-52074 Aachen, Germany
Grondal, C
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2005,
44
(08)
: 1210
-
1212
[9]
The dihydroxyacetone unit -: A versatile C3 building block in organic synthesis
Enders, D
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Enders, D
Voith, M
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Voith, M
Lenzen, A
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Lenzen, A
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2005,
44
(09)
: 1304
-
1325
[10]
Asymmetric synthesis of 2-amino-1,3-diols and D-erythro-sphinganine
Enders, D
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Enders, D
Müller-Hüwen, A
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
Müller-Hüwen, A
[J].
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,
2004,
2004
(08)
: 1732
-
1739
←
1
2
3
4
5
6
→