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乙二醇
甲醛
63148-62-9
MDI
丁酮
二甲基亚砜
碳酸氢钠
471-34-1
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乙二醇
甲醛
63148-62-9
MDI
丁酮
二甲基亚砜
碳酸氢钠
471-34-1
D-鞘氨醇
合成路线
（共 158 条）
178550-59-9
→
反应条件
123-78-4
D-鞘氨醇
反应条件
sodium hydroxide in ethanol 20 h; Heating;
参考文献
Shinozaki, Katsuo; Mizuno, Kazuhiro; Masaki, Yukio
Chemical and Pharmaceutical Bulletin, 1996 , vol. 44, # 5 p. 927 - 932
124-25-4
肉豆蔻醛
→
反应条件
123-78-4
D-鞘氨醇
反应条件
1.1: 2.7 g / LiOH*H2O; 4 Angstroem molecular sieves / tetrahydrofuran / 2.5 h / Heating 2.1: 59 percent / DIBALH / CH2Cl2; hexane / 1.5 h / -40 °C 3.1: 95 percent / NaH; Bu4NI / tetrahydrofuran / 48 h / Heating 4.1: 25 percent / Bu4NHSO4; Oxone; K2CO3 / 4,5-O-Me2C-3-oxo-THP-2-spiro-4'-2',2'-Me2-1',3'-dioxolan / acetonitrile; various solvent(s); H2O / 1.5 h 5.1: 98 percent / NH4OH / tetrahydrofuran / 2 h / 130 °C 6.1: 80 mg / PPh3; DIAD / tetrahydrofuran / 17 h / Heating 7.1: DIAD; TFA / CH2Cl2; H2O / 1.5 h / 20 °C 7.2: 1.7 mg / KOH / CH2Cl2; H2O / 0.5 h / Heating 8.1: 92 percent / Na; NH3 / diethyl ether / 5 h / -78 - 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 68, # 6 p. 2514 - 2517
59451-68-2
→
反应条件
123-78-4
D-鞘氨醇
反应条件
1.1: 59 percent / DIBALH / CH2Cl2; hexane / 1.5 h / -40 °C 2.1: 95 percent / NaH; Bu4NI / tetrahydrofuran / 48 h / Heating 3.1: 25 percent / Bu4NHSO4; Oxone; K2CO3 / 4,5-O-Me2C-3-oxo-THP-2-spiro-4'-2',2'-Me2-1',3'-dioxolan / acetonitrile; various solvent(s); H2O / 1.5 h 4.1: 98 percent / NH4OH / tetrahydrofuran / 2 h / 130 °C 5.1: 80 mg / PPh3; DIAD / tetrahydrofuran / 17 h / Heating 6.1: DIAD; TFA / CH2Cl2; H2O / 1.5 h / 20 °C 6.2: 1.7 mg / KOH / CH2Cl2; H2O / 0.5 h / Heating 7.1: 92 percent / Na; NH3 / diethyl ether / 5 h / -78 - 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 68, # 6 p. 2514 - 2517
93255-83-5
→
反应条件
123-78-4
D-鞘氨醇
反应条件
1.1: 95 percent / NaH; Bu4NI / tetrahydrofuran / 48 h / Heating 2.1: 25 percent / Bu4NHSO4; Oxone; K2CO3 / 4,5-O-Me2C-3-oxo-THP-2-spiro-4'-2',2'-Me2-1',3'-dioxolan / acetonitrile; various solvent(s); H2O / 1.5 h 3.1: 98 percent / NH4OH / tetrahydrofuran / 2 h / 130 °C 4.1: 80 mg / PPh3; DIAD / tetrahydrofuran / 17 h / Heating 5.1: DIAD; TFA / CH2Cl2; H2O / 1.5 h / 20 °C 5.2: 1.7 mg / KOH / CH2Cl2; H2O / 0.5 h / Heating 6.1: 92 percent / Na; NH3 / diethyl ether / 5 h / -78 - 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 68, # 6 p. 2514 - 2517
511542-09-9
→
反应条件
123-78-4
D-鞘氨醇
反应条件
1.1: 25 percent / Bu4NHSO4; Oxone; K2CO3 / 4,5-O-Me2C-3-oxo-THP-2-spiro-4'-2',2'-Me2-1',3'-dioxolan / acetonitrile; various solvent(s); H2O / 1.5 h 2.1: 98 percent / NH4OH / tetrahydrofuran / 2 h / 130 °C 3.1: 80 mg / PPh3; DIAD / tetrahydrofuran / 17 h / Heating 4.1: DIAD; TFA / CH2Cl2; H2O / 1.5 h / 20 °C 4.2: 1.7 mg / KOH / CH2Cl2; H2O / 0.5 h / Heating 5.1: 92 percent / Na; NH3 / diethyl ether / 5 h / -78 - 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 68, # 6 p. 2514 - 2517
331456-61-2
→
反应条件
123-78-4
D-鞘氨醇
反应条件
1.1: 80 percent / mCPBA; NaHCO3 / CH2Cl2 / 12 h / 0 - 20 °C 2.1: 89 percent / MeLi / tetrahydrofuran / 0.33 h / -78 °C 3.1: 82 percent / p-TsOH / CH2Cl2 / 2 h / 20 °C 4.1: 90 percent / Bu4NF / tetrahydrofuran / 12 h / 20 °C 5.1: NaH; 15-crown-5 / tetrahydrofuran / 14 h / Heating 5.2: 93 percent / Bu4NF / tetrahydrofuran 6.1: 59 percent / (PhO)2P(O)N3; DIAD; PPh3 / toluene / 12 h / 20 °C 7.1: 82 percent / p-TsOH / methanol / 12 h / 20 °C 8.1: Zn; NH4Cl / methanol / 12 h / 20 °C View Scheme
参考文献
Chemical communications (Cambridge, England), , # 5 p. 426 - 427
25791-20-2
正十四烷基三苯基溴化膦
→
反应条件
123-78-4
D-鞘氨醇
反应条件
1.1: PhLi / toluene / 0.75 h / -25 °C 1.2: 44 percent / toluene; tetrahydrofuran / 0.33 h / -25 °C 2.1: 86 percent / TEA / CH2Cl2 / 0.67 h 3.1: 21 percent / NaN3 / dimethylsulfoxide / 72 h / Heating 4.1: 96 percent / p-TsOH*H2O / CH2Cl2; methanol / 14 h 5.1: 95 percent / H2S; pyridine / H2O / 48 h View Scheme
参考文献
Chemistry and Physics of Lipids, , vol. 111, # 2 p. 111 - 138
3102-57-6
N-乙酰基神经鞘氨醇
→
反应条件
123-78-4
D-鞘氨醇
反应条件
hydrazine hydrate T=90°C; 20 h;
参考文献
Shibuya; Kawashima; Narita; Ikeda; Kitagawa
Chemical and Pharmaceutical Bulletin, 1992 , vol. 40, # 5 p. 1154 - 1165
117168-59-9
(2S,3S,4R)-2-叠氮基-1,3,4-十八烷三醇
→
反应条件
123-78-4
D-鞘氨醇
反应条件
1.1: 87 percent / triethylamine; 4-dimethylaminopyridine / CH2Cl2; dimethylformamide / 24 h / 20 °C 2.1: thionyl chloride; triethylamine / CH2Cl2 / 0.5 h / 0 °C 3.1: 1.09 g / sodium periodate; ruthenium(III) chloride trihydrate / CCl4; acetonitrile; H2O / 2 h / 20 °C 4.1: tetrabutylammonium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 2 h / Heating 4.2: 87 percent / sulfuric acid / toluene; tetrahydrofuran; H2O / 1 h / 20 °C 5.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C 6.1: 87 percent / sodium borohydride / propan-2-ol / 24 h / Heating View Scheme
参考文献
Journal of Organic Chemistry, , vol. 71, # 22 p. 8661 - 8664
157117-29-8
→
反应条件
123-78-4
D-鞘氨醇
反应条件
sodium hydroxide in ethanol T=95°C; 12 h; Yield given;
参考文献
Tetrahedron Letters, , vol. 35, # 5 p. 745 - 748
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