N-叔丁氧羰基-赤式-鞘氨醇合成路线 （共 43 条）
反应条件
1: 94 percent / Cu(I) thiophenecarboxylate; P(OEt)3 / Pd2(dba)3 / tetrahydrofuran / 10 h / 20 °C
2: 96 percent / LiAlH(O-t-Bu)3 / ethanol / 2 h / -78 °C
3: 99 percent / aq. HCl / methanol / 0.5 h / 20 °C
View Scheme
参考文献
Yang, Hao; Liebeskind, Lanny S.
Organic Letters, 2007 , vol. 9, # 16 p. 2993 - 2995
反应条件
1: -30 - 0 °C / pH 15
2: aq. AcOH / 5 h / 50 °C
View Scheme
参考文献
Murakami, Teiichi; Furusawa, Kiyotaka; Tamai, Tadakazu; Yoshikai, Kazuyoshi; Nishikawa, Masazumi
Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 4 p. 1115 - 1119
反应条件
1.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h
1.2: 86 percent / tetrahydrofuran; hexane / 1 h / -78 °C
2.1: 93 percent / lithium naphthalenide / tetrahydrofuran / 0.33 h / -78 °C
3.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C
3.2: 99 percent / tetrahydrofuran; toluene / 0.33 h / -23 °C
4.1: tributylamine; bis(acetato)bis(triphenylphosphine)palladium(II); formic acid / dimethylformamide / 7 h / 60 °C
5.1: 14 mg / tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h / 20 °C
View Scheme
参考文献
Nakamura, Tsuyoshi; Shiozaki, Masao
Tetrahedron, 2001 , vol. 57, # 44 p. 9087 - 9092
反应条件
1.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h
1.2: 86 percent / tetrahydrofuran; hexane / 1 h / -78 °C
2.1: 93 percent / lithium naphthalenide / tetrahydrofuran / 0.33 h / -78 °C
3.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C
3.2: 99 percent / tetrahydrofuran; toluene / 0.33 h / -23 °C
4.1: tributylamine; bis(acetato)bis(triphenylphosphine)palladium(II); formic acid / dimethylformamide / 7 h / 60 °C
5.1: 14 mg / tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h / 20 °C
View Scheme
参考文献
Nakamura, Tsuyoshi; Shiozaki, Masao
Tetrahedron, 2001 , vol. 57, # 44 p. 9087 - 9092
反应条件
1.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C
1.2: 99 percent / tetrahydrofuran; toluene / 0.33 h / -23 °C
2.1: tributylamine; bis(acetato)bis(triphenylphosphine)palladium(II); formic acid / dimethylformamide / 7 h / 60 °C
3.1: 14 mg / tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h / 20 °C
View Scheme
参考文献
Nakamura, Tsuyoshi; Shiozaki, Masao
Tetrahedron, 2001 , vol. 57, # 44 p. 9087 - 9092
反应条件
1: tributylamine; bis(acetato)bis(triphenylphosphine)palladium(II); formic acid / dimethylformamide / 7 h / 60 °C
2: 14 mg / tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h / 20 °C
View Scheme
参考文献
Nakamura, Tsuyoshi; Shiozaki, Masao
Tetrahedron, 2001 , vol. 57, # 44 p. 9087 - 9092
反应条件
1.1: 93 percent / lithium naphthalenide / tetrahydrofuran / 0.33 h / -78 °C
2.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C
2.2: 99 percent / tetrahydrofuran; toluene / 0.33 h / -23 °C
3.1: tributylamine; bis(acetato)bis(triphenylphosphine)palladium(II); formic acid / dimethylformamide / 7 h / 60 °C
4.1: 14 mg / tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h / 20 °C
View Scheme
参考文献
Nakamura, Tsuyoshi; Shiozaki, Masao
Tetrahedron, 2001 , vol. 57, # 44 p. 9087 - 9092
反应条件
1: 96 percent / LiAlH(O-t-Bu)3 / ethanol / 2 h / -78 °C
2: 99 percent / aq. HCl / methanol / 0.5 h / 20 °C
View Scheme
参考文献
Yang, Hao; Liebeskind, Lanny S.
Organic Letters, 2007 , vol. 9, # 16 p. 2993 - 2995
反应条件
1: 92 percent / TEA / tetrahydrofuran / 0.5 h / 20 °C
2: 97 percent / pyridine / dimethylformamide / 0.5 h / -40 °C
3: 99 percent / Ac2O; DMSO / 16 h / 20 °C
4: 89 percent / KHMDS / tetrahydrofuran; toluene / 3 h / -68 - -20 °C
5: 91 percent / HCOOH; TEA / Pd(OAc)2(triphenylphosphine)2 / dimethylformamide / 4 h / 60 °C
6: 100 percent / TBAF; AcOH / tetrahydrofuran / 1 h / 0 °C
View Scheme
参考文献
Van Den Berg, Richard J.B.H.N.; Korevaar, Cornelis G.N.; Van Der Marel, Gijsbert A.; Overkleeft, Herman S.; Van Boom, Jacques H.
Tetrahedron Letters, 2002 , vol. 43, # 46 p. 8409 - 8412
反应条件
1: 97 percent / pyridine / dimethylformamide / 0.5 h / -40 °C
2: 99 percent / Ac2O; DMSO / 16 h / 20 °C
3: 89 percent / KHMDS / tetrahydrofuran; toluene / 3 h / -68 - -20 °C
4: 91 percent / HCOOH; TEA / Pd(OAc)2(triphenylphosphine)2 / dimethylformamide / 4 h / 60 °C
5: 100 percent / TBAF; AcOH / tetrahydrofuran / 1 h / 0 °C
View Scheme
参考文献
Van Den Berg, Richard J.B.H.N.; Korevaar, Cornelis G.N.; Van Der Marel, Gijsbert A.; Overkleeft, Herman S.; Van Boom, Jacques H.
Tetrahedron Letters, 2002 , vol. 43, # 46 p. 8409 - 8412
