O-benzyloxy-N₁-benzyloxycarbonyl-ephedradine A

Base Information

• Chemical Name: O-benzyloxy-N₁-benzyloxycarbonyl-ephedradine A
• CAS No.: 566203-08-5
• Molecular Formula: C₄₃H₄₈N₄O₆
• Molecular Weight: 716.877
• Mol file: 566203-08-5.mol

Synonyms:O-benzyloxy-N₁-benzyloxycarbonyl-ephedradine A

Chemical Property of O-benzyloxy-N₁-benzyloxycarbonyl-ephedradine A

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-benzyloxy-N₁-benzyloxycarbonyl-ephedradine A

There total 41 articles about O-benzyloxy-N₁-benzyloxycarbonyl-ephedradine A which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

O-benzyloxy-N1-benzyloxycarbonyl-N2-nitrobenzenesulfonyl-ephedradine A (566202-88-8) → O-benzyloxy-N1-benzyloxycarbonyl-ephedradine A (566203-08-5)

Guidance literature:

With potassium hydroxide; thiophenol; In acetonitrile; at 50 ℃; for 1.16667h;

DOI:10.1021/ja036011k DOI:10.1016/j.tet.2004.06.144

Reference yield:

N-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-N-(3-hydroxy-propyl)-2-nitro-benzenesulfonamide (566202-76-4) → O-benzyloxy-N1-benzyloxycarbonyl-ephedradine A (566203-08-5)

Guidance literature:

Multi-step reaction with 25 steps

1: 96 percent / diethyl azodicarboxylate; PPh₃ / tetrahydrofuran; toluene / 0 - 20 °C

2: 88 percent / PhSH; K₂CO₃ / dimethylformamide; acetonitrile / 0.67 h / 50 °C

3: 67 percent / Me₂AlCl / CH₂Cl₂ / 3 h / Heating

4: 88 percent / pyridine / 0 - 20 °C

5: 84 percent / Pd(OAc)2; tris(o-tolyl)phosphine / dimethylformamide / 24 h / 100 °C

6: 66 percent / (DHQD)2PHAL; K₂OsO₂(OH)4 / propan-1-ol; H₂O / 4 h / 20 °C

7: 87 percent / CCl₄; PPh₃ / toluene / 2 h / 100 °C

8: ammonium formate / Pd/C / methanol / 1.25 h / 60 °C

9: 118 mg / diethyl azodicarboxylate; PPh₃ / toluene / 2 h / 60 °C

10: 72 percent / aq. Na₂CO₃ / CH₂Cl₂ / 4 h

11: 95 percent / diethyl azodicarboxylate; PPh₃ / toluene / 1 h / 60 °C

12: 93 percent / PhSH; aq. KOH / acetonitrile / 2 h / 60 °C

13: 91 percent / aq. NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

14: 94 percent / CSA / methanol / 0.33 h / 20 °C

15: 100 percent / diethyl azodicarboxylate; PPh₃ / toluene; tetrahydrofuran / 0 - 20 °C

16: 84 percent / aq. HF / acetonitrile / 1.5 h

17: 77 percent / diethyl azodicarboxylate; PPh₃ / toluene / 0 - 20 °C

18: 96 percent / K₂CO₃ / methanol; tetrahydrofuran / 1 h / 20 °C

19: Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

20: 77.9 mg / NaN₃ / dimethylformamide / 0.5 h / 60 °C

21: 97 percent / aq. LiOH / methanol; tetrahydrofuran / 5 h

22: 93 percent / WSCD*HCl / CH₂Cl₂ / 0 - 20 °C

23: PPh₃ / toluene / 4 h / Heating

24: 69.3 mg / H₂O / acetonitrile / 60 h / Heating

25: 75 percent / PhSH; aq. KOH / acetonitrile / 1.17 h / 50 °C

With pyridine; tetrachloromethane; palladium diacetate; potassium hydroxide; lithium hydroxide; sodium azide; potassium dioxotetrahydroxoosmate(VI); WSCD*HCl; camphor-10-sulfonic acid; hydrogen fluoride; water; ammonium formate; dimethylaluminum chloride; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; thiophenol; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; triphenylphosphine; tris-(o-tolyl)phosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; propan-1-ol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Mitsunobu reaction / 5: Heck reaction / 6: Sharpless aminohydroxylation / 9: Mitsunobu reaction / 11: Mitsunobu reaction / 15: Mitsunobu reaction / 17: Mitsunobu reaction;

DOI:10.1016/j.tet.2004.06.144

Reference yield:

(2R,3R)-2-(4-benzyloxyphenyl)-5-bromo-2,3-dihydrobenzofuran-3-carboxylic acid (566202-75-3) → O-benzyloxy-N1-benzyloxycarbonyl-ephedradine A (566203-08-5)

Guidance literature:

Multi-step reaction with 25 steps

1: 96 percent / diethyl azodicarboxylate; PPh₃ / tetrahydrofuran; toluene / 0 - 20 °C

2: 88 percent / PhSH; K₂CO₃ / dimethylformamide; acetonitrile / 0.67 h / 50 °C

3: 67 percent / Me₂AlCl / CH₂Cl₂ / 3 h / Heating

4: 88 percent / pyridine / 0 - 20 °C

5: 84 percent / Pd(OAc)2; tris(o-tolyl)phosphine / dimethylformamide / 24 h / 100 °C

6: 66 percent / (DHQD)2PHAL; K₂OsO₂(OH)4 / propan-1-ol; H₂O / 4 h / 20 °C

7: 87 percent / CCl₄; PPh₃ / toluene / 2 h / 100 °C

8: ammonium formate / Pd/C / methanol / 1.25 h / 60 °C

9: 118 mg / diethyl azodicarboxylate; PPh₃ / toluene / 2 h / 60 °C

10: 72 percent / aq. Na₂CO₃ / CH₂Cl₂ / 4 h

11: 95 percent / diethyl azodicarboxylate; PPh₃ / toluene / 1 h / 60 °C

12: 93 percent / PhSH; aq. KOH / acetonitrile / 2 h / 60 °C

13: 91 percent / aq. NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

14: 94 percent / CSA / methanol / 0.33 h / 20 °C

15: 100 percent / diethyl azodicarboxylate; PPh₃ / toluene; tetrahydrofuran / 0 - 20 °C

16: 84 percent / aq. HF / acetonitrile / 1.5 h

17: 77 percent / diethyl azodicarboxylate; PPh₃ / toluene / 0 - 20 °C

18: 96 percent / K₂CO₃ / methanol; tetrahydrofuran / 1 h / 20 °C

19: Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

20: 77.9 mg / NaN₃ / dimethylformamide / 0.5 h / 60 °C

21: 97 percent / aq. LiOH / methanol; tetrahydrofuran / 5 h

22: 93 percent / WSCD*HCl / CH₂Cl₂ / 0 - 20 °C

23: PPh₃ / toluene / 4 h / Heating

24: 69.3 mg / H₂O / acetonitrile / 60 h / Heating

25: 75 percent / PhSH; aq. KOH / acetonitrile / 1.17 h / 50 °C

With pyridine; tetrachloromethane; palladium diacetate; potassium hydroxide; lithium hydroxide; sodium azide; potassium dioxotetrahydroxoosmate(VI); WSCD*HCl; camphor-10-sulfonic acid; hydrogen fluoride; water; ammonium formate; dimethylaluminum chloride; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; thiophenol; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; triphenylphosphine; tris-(o-tolyl)phosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; propan-1-ol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Mitsunobu reaction / 5: Heck reaction / 6: Sharpless aminohydroxylation / 9: Mitsunobu reaction / 11: Mitsunobu reaction / 15: Mitsunobu reaction / 17: Mitsunobu reaction;

DOI:10.1016/j.tet.2004.06.144

upstream raw materials:

O-benzyloxy-N₁-benzyloxycarbonyl-N₂-nitrobenzenesulfonyl-ephedradine A

p-benzyloxybenzaldehyde

4-benzyloxybenzyl alcohol

4-hydroxy-benzaldehyde

Downstream raw materials:

(-)-ephedradine A