N-叔丁氧羰基-赤式-鞘氨醇合成路线 （共 43 条）
反应条件
1: 89 percent / KHMDS / tetrahydrofuran; toluene / 3 h / -68 - -20 °C
2: 91 percent / HCOOH; TEA / Pd(OAc)2(triphenylphosphine)2 / dimethylformamide / 4 h / 60 °C
3: 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: 99 percent / Ac2O; DMSO / 16 h / 20 °C
2: 89 percent / KHMDS / tetrahydrofuran; toluene / 3 h / -68 - -20 °C
3: 91 percent / HCOOH; TEA / Pd(OAc)2(triphenylphosphine)2 / dimethylformamide / 4 h / 60 °C
4: 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: 91 percent / HCOOH; TEA / Pd(OAc)2(triphenylphosphine)2 / dimethylformamide / 4 h / 60 °C
2: 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: pentadec-1-yne With Schwartz's reagent in tetrahydrofuran
T=20°C; 1 h;
2: (4S)-2,2-dimethyl-4-formyl-3-oxazolidine-carboxylic acid tert-butyl ester With zinc dibromide in tetrahydrofuran
T=20°C; 24 h;
3: With acetic acid in water
T=50°C; 5 h;
参考文献
Murakami, Teiichi; Furusawa, Kiyotaka
Tetrahedron, 2002 , vol. 58, # 45 p. 9257 - 9263
反应条件
1: 90 percent / p-TSA / methanol / 24 h / 20 °C
2: 70 percent / Red-Al / diethyl ether / 24 h / 20 °C
View Scheme
参考文献
Suzuki, Hikokazu; Mori, Michiko; Shibakami, Motonari
Synlett, 2003 , # 14 p. 2163 - 2166
反应条件
sodium hydrogencarbonate
参考文献
Qiao, Lixin; Kozikowski, Alan P.; Olivera, Ana; Spiegel, Sarah
Bioorganic and Medicinal Chemistry Letters, 1998 , vol. 8, # 7 p. 711 - 714
反应条件
1.1: tetrahydrofuran / 80 °C
1.2: 0.473 g / PhLi / tetrahydrofuran / 0.67 h
2.1: p-toluenesulfonic acid monohydrate / methanol / 4 h / 50 °C
3.1: aq. NaIO4 / CH2Cl2 / 0.75 h
4.1: 0.269 g / NaBH4 / methanol / 1 h / 0 °C
5.1: 92 percent / Bu4NF / tetrahydrofuran / 1 h / 20 °C
View Scheme
参考文献
Merino, Pedro; Jimenez, Pablo; Tejero, Tomas
Journal of Organic Chemistry, 2006 , vol. 71, # 12 p. 4685 - 4688
反应条件
1.1: DIBAL-H / tetrahydrofuran; hexane / 2 h / -78 °C
2.1: tetrahydrofuran / 80 °C
2.2: 0.473 g / PhLi / tetrahydrofuran / 0.67 h
3.1: p-toluenesulfonic acid monohydrate / methanol / 4 h / 50 °C
4.1: aq. NaIO4 / CH2Cl2 / 0.75 h
5.1: 0.269 g / NaBH4 / methanol / 1 h / 0 °C
6.1: 92 percent / Bu4NF / tetrahydrofuran / 1 h / 20 °C
View Scheme
参考文献
Merino, Pedro; Jimenez, Pablo; Tejero, Tomas
Journal of Organic Chemistry, 2006 , vol. 71, # 12 p. 4685 - 4688
反应条件
1: aq. NaIO4 / CH2Cl2 / 0.75 h
2: 0.269 g / NaBH4 / methanol / 1 h / 0 °C
3: 92 percent / Bu4NF / tetrahydrofuran / 1 h / 20 °C
View Scheme
参考文献
Merino, Pedro; Jimenez, Pablo; Tejero, Tomas
Journal of Organic Chemistry, 2006 , vol. 71, # 12 p. 4685 - 4688
反应条件
1: p-toluenesulfonic acid monohydrate / methanol / 4 h / 50 °C
2: aq. NaIO4 / CH2Cl2 / 0.75 h
3: 0.269 g / NaBH4 / methanol / 1 h / 0 °C
4: 92 percent / Bu4NF / tetrahydrofuran / 1 h / 20 °C
View Scheme
参考文献
Merino, Pedro; Jimenez, Pablo; Tejero, Tomas
Journal of Organic Chemistry, 2006 , vol. 71, # 12 p. 4685 - 4688
