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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
303053-06-7
合成路线
(共 7 条)
303053-06-7
→
反应条件
102989-24-2
(5S)-3-[(2S,13R)-2,13-二羟基-13-[(2R,5R)-5-[(2R,5R)-5-[(1R)-1-羟基十一烷基]四氢呋喃-2-基]四氢呋喃-2-基]十三烷基]-5-甲基-5H-呋喃-2-酮
反应条件
1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 2: 83 percent / AcCl / methanol; CH2Cl2 / 2 h / 20 °C View Scheme
参考文献
Avedissian, Hovsep; Sinna, Santosh C.; Yazbak, Ahmad; Sinha, Anjana; Neogi, Partha; Sinha, Subhash C.; Keinan, Ehud
Journal of Organic Chemistry, 2000 , vol. 65, # 19 p. 6035 - 6051
90269-57-1
→
反应条件
303053-06-7
反应条件
<b>Multi-step reaction with 18 steps<br /> </b>1.1: 9-BBN / tetrahydrofuran / 16 h / 0 - 20 °C<br />1.2: 42 percent / H<sub>2</sub>O<sub>2</sub>; NaOH / tetrahydrofuran; H<sub>2</sub>O / 1.5 h / 20 °C<br />2.1: 90 percent / PCC; celite / CH<sub>2</sub>Cl<sub>2</sub> / 2 h / 20 °C<br />3.1: KN(SiMe<sub>3</sub>)2 / toluene; tetrahydrofuran / 2 h / -78 - 0 °C<br />3.2: 95 percent / HMPA / tetrahydrofuran; toluene / 16 h / -78 - -5 °C<br />4.1: AD-mix-β; MeSO<sub>2</sub>NH<sub>2</sub> / 2-methyl-propan-2-ol; H<sub>2</sub>O / 16 h / 0 °C<br />5.1: KOH / H<sub>2</sub>O; methanol / 60 °C<br />6.1: 2.12 g / TsOH / CH<sub>2</sub>Cl<sub>2</sub> / 0.5 h / 20 °C<br />7.1: 68 percent / Re<sub>2</sub>O<sub>7</sub>; 2,6-lutidine / CH<sub>2</sub>Cl<sub>2</sub> / 8 h / 20 °C<br />8.1: 92 percent / H<sub>2</sub>; Et<sub>3</sub>N / Lindlar catalyst / hexane; various solvent(s) / 16 h / -10 - -4 °C<br />9.1: 71 percent / Et<sub>3</sub>N / CH<sub>2</sub>Cl<sub>2</sub> / 1 h / 0 °C<br />10.1: 92 percent / AD-mix-β; MeSO<sub>2</sub>NH<sub>2</sub> / 2-methyl-propan-2-ol; H<sub>2</sub>O / 0 °C<br />11.1: 81 percent / pyridine / 3 h / Heating<br />12.1: 100 percent / LiAlH<sub>4</sub> / diethyl ether / 2 h / Heating<br />13.1: diisopropylethylamine; DMAP / CH<sub>2</sub>Cl<sub>2</sub> / 6 h / 20 °C<br />14.1: 508 mg / diisopropylethylamine / CH<sub>2</sub>Cl<sub>2</sub> / 12 h<br />15.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C<br />16.1: 86 percent / I<sub>2</sub>; Ph<sub>3</sub>P; imidazole / CH<sub>2</sub>Cl<sub>2</sub> / 1 h / 20 °C<br />17.1: 85 percent / NaHCO<sub>3</sub> / acetonitrile / 36 h / 40 °C<br />18.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling<br />18.2: 60 percent / tetrahydrofuran; hexane / 0.25 h<br /> <br />
参考文献
Avedissian, Hovsep; Sinna, Santosh C.; Yazbak, Ahmad; Sinha, Anjana; Neogi, Partha; Sinha, Subhash C.; Keinan, Ehud Journal of Organic Chemistry, 2000 , vol. 65, # 19 p. 6035 - 6051
131618-60-5
→
反应条件
303053-06-7
反应条件
<b>Multi-step reaction with 21 steps<br /> </b>1.1: 75 percent / PPh<sub>3</sub> / CH<sub>2</sub>Cl<sub>2</sub> / 0.17 h / 0 °C<br />2.1: tetrahydrofuran / 2.5 h / -78 - 0 °C<br />2.2: 70 percent / HMPA / tetrahydrofuran / -78 - 20 °C<br />3.1: 74 percent / AcOH / H<sub>2</sub>O / 16 h / 100 °C<br />4.1: 78 percent / tetrahydrofuran / -20 °C<br />5.1: 88 percent / propionic acid / 2 h / Heating<br />6.1: AD-mix-β; MeSO<sub>2</sub>NH<sub>2</sub> / 2-methyl-propan-2-ol; H<sub>2</sub>O / 16 h / 0 °C<br />7.1: KOH / H<sub>2</sub>O; methanol / 2 h / 60 °C<br />8.1: 1.5 g / TsOH / CH<sub>2</sub>Cl<sub>2</sub> / 1 h / 20 °C<br />9.1: 95 percent / TsOH / acetone / 0.5 h / 20 °C<br />10.1: 95 percent / H<sub>2</sub>; Et<sub>3</sub>N / Lindlar catalyst / hexane; various solvent(s) / 12 h<br />11.1: 64 percent / Re<sub>2</sub>O<sub>7</sub>; 2,6-lutidine / CH<sub>2</sub>Cl<sub>2</sub> / 20 °C<br />12.1: 94 percent / Et<sub>3</sub>N / CH<sub>2</sub>Cl<sub>2</sub> / 0.5 h / -30 °C<br />13.1: 90 percent / TsOH / H<sub>2</sub>O; methanol / 16 h / 20 °C<br />14.1: 81 percent / pyridine / 3 h / Heating<br />15.1: 100 percent / LiAlH<sub>4</sub> / diethyl ether / 2 h / Heating<br />16.1: diisopropylethylamine; DMAP / CH<sub>2</sub>Cl<sub>2</sub> / 6 h / 20 °C<br />17.1: 508 mg / diisopropylethylamine / CH<sub>2</sub>Cl<sub>2</sub> / 12 h<br />18.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C<br />19.1: 86 percent / I<sub>2</sub>; Ph<sub>3</sub>P; imidazole / CH<sub>2</sub>Cl<sub>2</sub> / 1 h / 20 °C<br />20.1: 85 percent / NaHCO<sub>3</sub> / acetonitrile / 36 h / 40 °C<br />21.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling<br />21.2: 60 percent / tetrahydrofuran; hexane / 0.25 h<br /> <br />
参考文献
Avedissian, Hovsep; Sinna, Santosh C.; Yazbak, Ahmad; Sinha, Anjana; Neogi, Partha; Sinha, Subhash C.; Keinan, Ehud Journal of Organic Chemistry, 2000 , vol. 65, # 19 p. 6035 - 6051
160667-50-5
→
反应条件
303053-06-7
反应条件
<b>Multi-step reaction with 16 steps<br /> </b>1.1: KN(SiMe<sub>3</sub>)2 / toluene; tetrahydrofuran / 2 h / -78 - 0 °C<br />1.2: 95 percent / HMPA / tetrahydrofuran; toluene / 16 h / -78 - -5 °C<br />2.1: AD-mix-β; MeSO<sub>2</sub>NH<sub>2</sub> / 2-methyl-propan-2-ol; H<sub>2</sub>O / 16 h / 0 °C<br />3.1: KOH / H<sub>2</sub>O; methanol / 60 °C<br />4.1: 2.12 g / TsOH / CH<sub>2</sub>Cl<sub>2</sub> / 0.5 h / 20 °C<br />5.1: 68 percent / Re<sub>2</sub>O<sub>7</sub>; 2,6-lutidine / CH<sub>2</sub>Cl<sub>2</sub> / 8 h / 20 °C<br />6.1: 92 percent / H<sub>2</sub>; Et<sub>3</sub>N / Lindlar catalyst / hexane; various solvent(s) / 16 h / -10 - -4 °C<br />7.1: 71 percent / Et<sub>3</sub>N / CH<sub>2</sub>Cl<sub>2</sub> / 1 h / 0 °C<br />8.1: 92 percent / AD-mix-β; MeSO<sub>2</sub>NH<sub>2</sub> / 2-methyl-propan-2-ol; H<sub>2</sub>O / 0 °C<br />9.1: 81 percent / pyridine / 3 h / Heating<br />10.1: 100 percent / LiAlH<sub>4</sub> / diethyl ether / 2 h / Heating<br />11.1: diisopropylethylamine; DMAP / CH<sub>2</sub>Cl<sub>2</sub> / 6 h / 20 °C<br />12.1: 508 mg / diisopropylethylamine / CH<sub>2</sub>Cl<sub>2</sub> / 12 h<br />13.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C<br />14.1: 86 percent / I<sub>2</sub>; Ph<sub>3</sub>P; imidazole / CH<sub>2</sub>Cl<sub>2</sub> / 1 h / 20 °C<br />15.1: 85 percent / NaHCO<sub>3</sub> / acetonitrile / 36 h / 40 °C<br />16.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling<br />16.2: 60 percent / tetrahydrofuran; hexane / 0.25 h<br /> <br />
参考文献
Avedissian, Hovsep; Sinna, Santosh C.; Yazbak, Ahmad; Sinha, Anjana; Neogi, Partha; Sinha, Subhash C.; Keinan, Ehud Journal of Organic Chemistry, 2000 , vol. 65, # 19 p. 6035 - 6051
172667-61-7
→
反应条件
303053-06-7
反应条件
<b>Multi-step reaction with 15 steps<br /> </b>1.1: AD-mix-β; MeSO<sub>2</sub>NH<sub>2</sub> / 2-methyl-propan-2-ol; H<sub>2</sub>O / 16 h / 0 °C<br />2.1: KOH / H<sub>2</sub>O; methanol / 60 °C<br />3.1: 2.12 g / TsOH / CH<sub>2</sub>Cl<sub>2</sub> / 0.5 h / 20 °C<br />4.1: 68 percent / Re<sub>2</sub>O<sub>7</sub>; 2,6-lutidine / CH<sub>2</sub>Cl<sub>2</sub> / 8 h / 20 °C<br />5.1: 92 percent / H<sub>2</sub>; Et<sub>3</sub>N / Lindlar catalyst / hexane; various solvent(s) / 16 h / -10 - -4 °C<br />6.1: 71 percent / Et<sub>3</sub>N / CH<sub>2</sub>Cl<sub>2</sub> / 1 h / 0 °C<br />7.1: 92 percent / AD-mix-β; MeSO<sub>2</sub>NH<sub>2</sub> / 2-methyl-propan-2-ol; H<sub>2</sub>O / 0 °C<br />8.1: 81 percent / pyridine / 3 h / Heating<br />9.1: 100 percent / LiAlH<sub>4</sub> / diethyl ether / 2 h / Heating<br />10.1: diisopropylethylamine; DMAP / CH<sub>2</sub>Cl<sub>2</sub> / 6 h / 20 °C<br />11.1: 508 mg / diisopropylethylamine / CH<sub>2</sub>Cl<sub>2</sub> / 12 h<br />12.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C<br />13.1: 86 percent / I<sub>2</sub>; Ph<sub>3</sub>P; imidazole / CH<sub>2</sub>Cl<sub>2</sub> / 1 h / 20 °C<br />14.1: 85 percent / NaHCO<sub>3</sub> / acetonitrile / 36 h / 40 °C<br />15.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling<br />15.2: 60 percent / tetrahydrofuran; hexane / 0.25 h<br /> <br />
参考文献
Avedissian, Hovsep; Sinna, Santosh C.; Yazbak, Ahmad; Sinha, Anjana; Neogi, Partha; Sinha, Subhash C.; Keinan, Ehud Journal of Organic Chemistry, 2000 , vol. 65, # 19 p. 6035 - 6051
62992-46-5
2-(4-戊炔氧基)四氢-2H-吡喃
→
反应条件
303053-06-7
反应条件
<b>Multi-step reaction with 20 steps<br /> </b>1.1: nBuLi / tetrahydrofuran / 2 h / -78 - 0 °C<br />2.1: 9.95 g / p-TsOH / methanol; H<sub>2</sub>O / 1 h / 20 °C<br />3.1: 91 percent / I<sub>2</sub>; imidazole; PPh<sub>3</sub> / toluene / 2 h / 20 °C<br />4.1: 99 percent / acetonitrile / 16 h / Heating<br />5.1: KN(SiMe<sub>3</sub>)2 / toluene; tetrahydrofuran / 2 h / -78 - 0 °C<br />5.2: 95 percent / HMPA / tetrahydrofuran; toluene / 16 h / -78 - -5 °C<br />6.1: AD-mix-β; MeSO<sub>2</sub>NH<sub>2</sub> / 2-methyl-propan-2-ol; H<sub>2</sub>O / 16 h / 0 °C<br />7.1: KOH / H<sub>2</sub>O; methanol / 60 °C<br />8.1: 2.12 g / TsOH / CH<sub>2</sub>Cl<sub>2</sub> / 0.5 h / 20 °C<br />9.1: 68 percent / Re<sub>2</sub>O<sub>7</sub>; 2,6-lutidine / CH<sub>2</sub>Cl<sub>2</sub> / 8 h / 20 °C<br />10.1: 92 percent / H<sub>2</sub>; Et<sub>3</sub>N / Lindlar catalyst / hexane; various solvent(s) / 16 h / -10 - -4 °C<br />11.1: 71 percent / Et<sub>3</sub>N / CH<sub>2</sub>Cl<sub>2</sub> / 1 h / 0 °C<br />12.1: 92 percent / AD-mix-β; MeSO<sub>2</sub>NH<sub>2</sub> / 2-methyl-propan-2-ol; H<sub>2</sub>O / 0 °C<br />13.1: 81 percent / pyridine / 3 h / Heating<br />14.1: 100 percent / LiAlH<sub>4</sub> / diethyl ether / 2 h / Heating<br />15.1: diisopropylethylamine; DMAP / CH<sub>2</sub>Cl<sub>2</sub> / 6 h / 20 °C<br />16.1: 508 mg / diisopropylethylamine / CH<sub>2</sub>Cl<sub>2</sub> / 12 h<br />17.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C<br />18.1: 86 percent / I<sub>2</sub>; Ph<sub>3</sub>P; imidazole / CH<sub>2</sub>Cl<sub>2</sub> / 1 h / 20 °C<br />19.1: 85 percent / NaHCO<sub>3</sub> / acetonitrile / 36 h / 40 °C<br />20.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling<br />20.2: 60 percent / tetrahydrofuran; hexane / 0.25 h<br /> <br />
参考文献
Avedissian, Hovsep; Sinna, Santosh C.; Yazbak, Ahmad; Sinha, Anjana; Neogi, Partha; Sinha, Subhash C.; Keinan, Ehud Journal of Organic Chemistry, 2000 , vol. 65, # 19 p. 6035 - 6051
5390-04-5
4-戊炔-1-醇
→
反应条件
303053-06-7
反应条件
<b>Multi-step reaction with 21 steps<br /> </b>1.1: 96 percent / p-TsOH / diethyl ether / 2 h / 20 °C<br />2.1: nBuLi / tetrahydrofuran / 2 h / -78 - 0 °C<br />3.1: 9.95 g / p-TsOH / methanol; H<sub>2</sub>O / 1 h / 20 °C<br />4.1: 91 percent / I<sub>2</sub>; imidazole; PPh<sub>3</sub> / toluene / 2 h / 20 °C<br />5.1: 99 percent / acetonitrile / 16 h / Heating<br />6.1: KN(SiMe<sub>3</sub>)2 / toluene; tetrahydrofuran / 2 h / -78 - 0 °C<br />6.2: 95 percent / HMPA / tetrahydrofuran; toluene / 16 h / -78 - -5 °C<br />7.1: AD-mix-β; MeSO<sub>2</sub>NH<sub>2</sub> / 2-methyl-propan-2-ol; H<sub>2</sub>O / 16 h / 0 °C<br />8.1: KOH / H<sub>2</sub>O; methanol / 60 °C<br />9.1: 2.12 g / TsOH / CH<sub>2</sub>Cl<sub>2</sub> / 0.5 h / 20 °C<br />10.1: 68 percent / Re<sub>2</sub>O<sub>7</sub>; 2,6-lutidine / CH<sub>2</sub>Cl<sub>2</sub> / 8 h / 20 °C<br />11.1: 92 percent / H<sub>2</sub>; Et<sub>3</sub>N / Lindlar catalyst / hexane; various solvent(s) / 16 h / -10 - -4 °C<br />12.1: 71 percent / Et<sub>3</sub>N / CH<sub>2</sub>Cl<sub>2</sub> / 1 h / 0 °C<br />13.1: 92 percent / AD-mix-β; MeSO<sub>2</sub>NH<sub>2</sub> / 2-methyl-propan-2-ol; H<sub>2</sub>O / 0 °C<br />14.1: 81 percent / pyridine / 3 h / Heating<br />15.1: 100 percent / LiAlH<sub>4</sub> / diethyl ether / 2 h / Heating<br />16.1: diisopropylethylamine; DMAP / CH<sub>2</sub>Cl<sub>2</sub> / 6 h / 20 °C<br />17.1: 508 mg / diisopropylethylamine / CH<sub>2</sub>Cl<sub>2</sub> / 12 h<br />18.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C<br />19.1: 86 percent / I<sub>2</sub>; Ph<sub>3</sub>P; imidazole / CH<sub>2</sub>Cl<sub>2</sub> / 1 h / 20 °C<br />20.1: 85 percent / NaHCO<sub>3</sub> / acetonitrile / 36 h / 40 °C<br />21.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling<br />21.2: 60 percent / tetrahydrofuran; hexane / 0.25 h<br /> <br />
参考文献
Avedissian, Hovsep; Sinna, Santosh C.; Yazbak, Ahmad; Sinha, Anjana; Neogi, Partha; Sinha, Subhash C.; Keinan, Ehud Journal of Organic Chemistry, 2000 , vol. 65, # 19 p. 6035 - 6051