(2S,4R)-5-苄基氧基羰基氨基-2-叔丁氧羰基氨基-4-三异丙基硅烷基氧基-戊酸合成路线 （共 9 条）
反应条件
2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium chlorite; sodium phosphate buffer; sodium hypochlorite in acetonitrile
T=35°C; pH=6.7; 4.5 h;
参考文献
LUDWIG-MAXIMILIANS-UNIVERSITAET MUENCHEN
Patent: WO2006/94770 A2, 2006 ;
Location in patent: Page/Page column 10; 19 ;
反应条件
1.1: 14.64 g / silica gel / CH2Cl2; H2O / 72 h / 20 °C
2.1: 97 percent / DMSO; oxalyl chloride; Et3N / CH2Cl2 / 1.5 h / -60 - 20 °C
3.1: Cu(OAc)2*H2O; 2,2-bis[(3aS,8aR)-3a,8,8a-3H-indeno[3,2-d]oxazol-2yl]propane / ethanol / 120 h / 20 °C
3.2: 2,6-lutidine / CH2Cl2 / 16.5 h / 0 - 20 °C
3.3: HCO2NH4 / Pd/C / methanol / 24 h / 20 °C
4.1: 2.252 g / Et3N / CH2Cl2 / 70 h / 20 °C
5.1: 64 percent / (+/-)-camphorsulfonic acid; ethylene glycol / tetrahydrofuran / 48 h / 50 °C
6.1: 83 percent / TEMPO; sodium phosphate buffer; aq. NaClO2 / aq. NaOCl / acetonitrile / 4.5 h / 35 °C / pH 6.7
View Scheme
参考文献
Paintner, Franz F.; Allmendinger, Lars; Bauschke, Gerd; Klemann, Patricia
Organic Letters, 2005 , vol. 7, # 7 p. 1423 - 1426
反应条件
1: 64 percent / (+/-)-camphorsulfonic acid; ethylene glycol / tetrahydrofuran / 48 h / 50 °C
2: 83 percent / TEMPO; sodium phosphate buffer; aq. NaClO2 / aq. NaOCl / acetonitrile / 4.5 h / 35 °C / pH 6.7
View Scheme
参考文献
Paintner, Franz F.; Allmendinger, Lars; Bauschke, Gerd; Klemann, Patricia
Organic Letters, 2005 , vol. 7, # 7 p. 1423 - 1426
反应条件
1.1: 98 percent / Et3N / H2O; dioxane
2.1: 97 percent / NaBH4 / ethanol / Heating
3.1: p-toluenesulfonic acid monohydrate / CH2Cl2 / 2 h / 20 °C
3.2: 67 h / 20 °C
4.1: 14.64 g / silica gel / CH2Cl2; H2O / 72 h / 20 °C
5.1: 97 percent / DMSO; oxalyl chloride; Et3N / CH2Cl2 / 1.5 h / -60 - 20 °C
6.1: Cu(OAc)2*H2O; 2,2-bis[(3aS,8aR)-3a,8,8a-3H-indeno[3,2-d]oxazol-2yl]propane / ethanol / 120 h / 20 °C
6.2: 2,6-lutidine / CH2Cl2 / 16.5 h / 0 - 20 °C
6.3: HCO2NH4 / Pd/C / methanol / 24 h / 20 °C
7.1: 2.252 g / Et3N / CH2Cl2 / 70 h / 20 °C
8.1: 64 percent / (+/-)-camphorsulfonic acid; ethylene glycol / tetrahydrofuran / 48 h / 50 °C
9.1: 83 percent / TEMPO; sodium phosphate buffer; aq. NaClO2 / aq. NaOCl / acetonitrile / 4.5 h / 35 °C / pH 6.7
View Scheme
参考文献
Paintner, Franz F.; Allmendinger, Lars; Bauschke, Gerd; Klemann, Patricia
Organic Letters, 2005 , vol. 7, # 7 p. 1423 - 1426
反应条件
1.1: Cu(OAc)2*H2O; 2,2-bis[(3aS,8aR)-3a,8,8a-3H-indeno[3,2-d]oxazol-2yl]propane / ethanol / 120 h / 20 °C
1.2: 2,6-lutidine / CH2Cl2 / 16.5 h / 0 - 20 °C
1.3: HCO2NH4 / Pd/C / methanol / 24 h / 20 °C
2.1: 2.252 g / Et3N / CH2Cl2 / 70 h / 20 °C
3.1: 64 percent / (+/-)-camphorsulfonic acid; ethylene glycol / tetrahydrofuran / 48 h / 50 °C
4.1: 83 percent / TEMPO; sodium phosphate buffer; aq. NaClO2 / aq. NaOCl / acetonitrile / 4.5 h / 35 °C / pH 6.7
View Scheme
参考文献
Paintner, Franz F.; Allmendinger, Lars; Bauschke, Gerd; Klemann, Patricia
Organic Letters, 2005 , vol. 7, # 7 p. 1423 - 1426
反应条件
1.1: p-toluenesulfonic acid monohydrate / CH2Cl2 / 2 h / 20 °C
1.2: 67 h / 20 °C
2.1: 14.64 g / silica gel / CH2Cl2; H2O / 72 h / 20 °C
3.1: 97 percent / DMSO; oxalyl chloride; Et3N / CH2Cl2 / 1.5 h / -60 - 20 °C
4.1: Cu(OAc)2*H2O; 2,2-bis[(3aS,8aR)-3a,8,8a-3H-indeno[3,2-d]oxazol-2yl]propane / ethanol / 120 h / 20 °C
4.2: 2,6-lutidine / CH2Cl2 / 16.5 h / 0 - 20 °C
4.3: HCO2NH4 / Pd/C / methanol / 24 h / 20 °C
5.1: 2.252 g / Et3N / CH2Cl2 / 70 h / 20 °C
6.1: 64 percent / (+/-)-camphorsulfonic acid; ethylene glycol / tetrahydrofuran / 48 h / 50 °C
7.1: 83 percent / TEMPO; sodium phosphate buffer; aq. NaClO2 / aq. NaOCl / acetonitrile / 4.5 h / 35 °C / pH 6.7
View Scheme
参考文献
Paintner, Franz F.; Allmendinger, Lars; Bauschke, Gerd; Klemann, Patricia
Organic Letters, 2005 , vol. 7, # 7 p. 1423 - 1426
反应条件
1.1: 97 percent / NaBH4 / ethanol / Heating
2.1: p-toluenesulfonic acid monohydrate / CH2Cl2 / 2 h / 20 °C
2.2: 67 h / 20 °C
3.1: 14.64 g / silica gel / CH2Cl2; H2O / 72 h / 20 °C
4.1: 97 percent / DMSO; oxalyl chloride; Et3N / CH2Cl2 / 1.5 h / -60 - 20 °C
5.1: Cu(OAc)2*H2O; 2,2-bis[(3aS,8aR)-3a,8,8a-3H-indeno[3,2-d]oxazol-2yl]propane / ethanol / 120 h / 20 °C
5.2: 2,6-lutidine / CH2Cl2 / 16.5 h / 0 - 20 °C
5.3: HCO2NH4 / Pd/C / methanol / 24 h / 20 °C
6.1: 2.252 g / Et3N / CH2Cl2 / 70 h / 20 °C
7.1: 64 percent / (+/-)-camphorsulfonic acid; ethylene glycol / tetrahydrofuran / 48 h / 50 °C
8.1: 83 percent / TEMPO; sodium phosphate buffer; aq. NaClO2 / aq. NaOCl / acetonitrile / 4.5 h / 35 °C / pH 6.7
View Scheme
参考文献
Paintner, Franz F.; Allmendinger, Lars; Bauschke, Gerd; Klemann, Patricia
Organic Letters, 2005 , vol. 7, # 7 p. 1423 - 1426
反应条件
1.1: 97 percent / DMSO; oxalyl chloride; Et3N / CH2Cl2 / 1.5 h / -60 - 20 °C
2.1: Cu(OAc)2*H2O; 2,2-bis[(3aS,8aR)-3a,8,8a-3H-indeno[3,2-d]oxazol-2yl]propane / ethanol / 120 h / 20 °C
2.2: 2,6-lutidine / CH2Cl2 / 16.5 h / 0 - 20 °C
2.3: HCO2NH4 / Pd/C / methanol / 24 h / 20 °C
3.1: 2.252 g / Et3N / CH2Cl2 / 70 h / 20 °C
4.1: 64 percent / (+/-)-camphorsulfonic acid; ethylene glycol / tetrahydrofuran / 48 h / 50 °C
5.1: 83 percent / TEMPO; sodium phosphate buffer; aq. NaClO2 / aq. NaOCl / acetonitrile / 4.5 h / 35 °C / pH 6.7
View Scheme
参考文献
Paintner, Franz F.; Allmendinger, Lars; Bauschke, Gerd; Klemann, Patricia
Organic Letters, 2005 , vol. 7, # 7 p. 1423 - 1426
反应条件
1.1: Cu(OAc)2*H2O; 2,2-bis[(3aS,8aR)-3a,8,8a-3H-indeno[3,2-d]oxazol-2yl]propane / ethanol / 120 h / 20 °C
1.2: 2,6-lutidine / CH2Cl2 / 16.5 h / 0 - 20 °C
1.3: HCO2NH4 / Pd/C / methanol / 24 h / 20 °C
2.1: 2.252 g / Et3N / CH2Cl2 / 70 h / 20 °C
3.1: 64 percent / (+/-)-camphorsulfonic acid; ethylene glycol / tetrahydrofuran / 48 h / 50 °C
4.1: 83 percent / TEMPO; sodium phosphate buffer; aq. NaClO2 / aq. NaOCl / acetonitrile / 4.5 h / 35 °C / pH 6.7
View Scheme
参考文献
Paintner, Franz F.; Allmendinger, Lars; Bauschke, Gerd; Klemann, Patricia
Organic Letters, 2005 , vol. 7, # 7 p. 1423 - 1426
