6(S),19-(N,N'-phthalhydrazido)-3β-acetoxy-9,10-secoergosta-5(10),7(E),22(E)-triene

Base Information

• Chemical Name: 6(S),19-(N,N'-phthalhydrazido)-3β-acetoxy-9,10-secoergosta-5(10),7(E),22(E)-triene
• CAS No.: 87417-00-3
• Molecular Formula: C₃₈H₅₀N₂O₄
• Molecular Weight: 598.826
• Mol file: 87417-00-3.mol

Synonyms:6(S),19-(N,N'-phthalhydrazido)-3β-acetoxy-9,10-secoergosta-5(10),7(E),22(E)-triene

Chemical Property of 6(S),19-(N,N'-phthalhydrazido)-3β-acetoxy-9,10-secoergosta-5(10),7(E),22(E)-triene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6(S),19-(N,N'-phthalhydrazido)-3β-acetoxy-9,10-secoergosta-5(10),7(E),22(E)-triene

There total 1 articles about 6(S),19-(N,N'-phthalhydrazido)-3β-acetoxy-9,10-secoergosta-5(10),7(E),22(E)-triene 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: 54.0%

2,3-dihydrophthalazine-1,4-dione (1445-69-8) + ergocalciferol acetate (2579-08-0) → 6(R),19-(N,N'-phthalhydrazido)-3β-acetoxy-9,10-secoergosta-5(10),7(E),22(E)-triene (87480-21-5,169737-23-9) + 6(S),19-(N,N'-phthalhydrazido)-3β-acetoxy-9,10-secoergosta-5(10),7(E),22(E)-triene (87417-00-3,169737-23-9)

Guidance literature:

With lead(IV) acetate; acetic acid; In dichloromethane; at 0 ℃;

DOI:10.1021/jo00375a013

Reference yield:

6(S),19-(N,N'-phthalhydrazido)-3β-acetoxy-9,10-secoergosta-5(10),7(E),22(E)-triene (87417-00-3,169737-23-9) → calcidiol (19356-17-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) O₃, 2.) triphenylphosphine / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C, 30 min

2: 1.) phenyllithium / 1.) THF, 2.) benzene, THF, 3 min

3: 85 percent / aq. acetic acid / tetrahydrofuran / 15 h

4: H₂, NaHCO₃; / 5percent Pt/C / benzene; ethanol / 24 h

5: NaOH / benzene; methanol / 0.33 h / Ambient temperature

6: 1.) hydrazine, 2.) dianisyl telluroxide / 1.) ethanol, reflux, overnight, 2.) water, CH₂Cl₂, 1,2-dibromotetrachloroethane, 5 h

7: 82 percent / triethylamine, anthracene / benzene / 1 h / Irradiation

With sodium hydroxide; anthracene; di-(p-methoxyphenyl)tellurium oxide; hydrogen; sodium hydrogencarbonate; ozone; acetic acid; phenyllithium; triethylamine; triphenylphosphine; hydrazine; platinum on activated charcoal; In tetrahydrofuran; methanol; ethanol; benzene;

DOI:10.1021/jo00375a013

Reference yield:

6(S),19-(N,N'-phthalhydrazido)-3β-acetoxy-9,10-secoergosta-5(10),7(E),22(E)-triene (87417-00-3,169737-23-9) → 3,5-Dinitro-benzoic acid (S)-3-[2-[(1R,3aS,7aR)-1-((R)-5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(E)-ylidene]-4-methylene-cyclohexyl ester (87417-20-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) O₃, 2.) triphenylphosphine / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C, 30 min

2: 1.) phenyllithium / 1.) THF, 2.) benzene, THF, 3 min

3: 85 percent / aq. acetic acid / tetrahydrofuran / 15 h

4: H₂, NaHCO₃; / 5percent Pt/C / benzene; ethanol / 24 h

5: NaOH / benzene; methanol / 0.33 h / Ambient temperature

6: 1.) hydrazine, 2.) dianisyl telluroxide / 1.) ethanol, reflux, overnight, 2.) water, CH₂Cl₂, 1,2-dibromotetrachloroethane, 5 h

7: 70 percent / pyridine

With pyridine; sodium hydroxide; di-(p-methoxyphenyl)tellurium oxide; hydrogen; sodium hydrogencarbonate; ozone; acetic acid; phenyllithium; triphenylphosphine; hydrazine; platinum on activated charcoal; In tetrahydrofuran; methanol; ethanol; benzene;

DOI:10.1021/jo00375a013

upstream raw materials:

2,3-dihydrophthalazine-1,4-dione

ergocalciferol acetate

Downstream raw materials:

calcidiol

3,5-Dinitro-benzoic acid (S)-3-[2-[(1R,3aS,7aR)-1-((R)-5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(E)-ylidene]-4-methylene-cyclohexyl ester

3β,25-dihydroxy-9,10-secocholesta-5(E),7(E),10(19)-triene