(5Z,7E)-2-oxa-9,10-seco-5,7,10(19)-cholestatrien-25-ol

Base Information

• Chemical Name: (5Z,7E)-2-oxa-9,10-seco-5,7,10(19)-cholestatrien-25-ol
• CAS No.: 113490-39-4
• Molecular Formula: C₂₆H₄₂O₂
• Molecular Weight: 386.618
• Nikkaji Number: J401.188K
• Metabolomics Workbench ID: 35591
• Mol file: 113490-39-4.mol

Synonyms:2-oxa-3-deoxy-25-hydroxyvitamin D3;2-oxa-3-deoxy-25-OH-D3

Chemical Property of (5Z,7E)-2-oxa-9,10-seco-5,7,10(19)-cholestatrien-25-ol

Chemical Property:

• Vapor Pressure: 3.31E-12mmHg at 25°C
• Boiling Point: 502.6°Cat760mmHg
• Flash Point: 205.8°C
• PSA: 29.46000
• Density: 1g/cm³
• LogP: 6.60940
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 386.318480578
• Heavy Atom Count: 28
• Complexity: 626

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCCC(C)(C)O)C1CCC2C1(CCCC2=CC=C3CCOCC3=C)C
• Isomeric SMILES: C[C@H](CCCC(C)(C)O)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\CCOCC3=C)C

Technology Process of (5Z,7E)-2-oxa-9,10-seco-5,7,10(19)-cholestatrien-25-ol

There total 10 articles about (5Z,7E)-2-oxa-9,10-seco-5,7,10(19)-cholestatrien-25-ol 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:

pent-3-yn-1-ol (10229-10-4) → 25-hydroxy-3-deoxy-2-oxavitamin D3 (113490-39-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 87 percent / p-toluenesulfonic acid / benzene / 12 h / Heating

2: 11 percent / 570 °C / 30 Torr

3: 81 percent / Et₃N, Pd(PPh₃)2Cl₂ / dimethylformamide / 4.5 h / 75 °C

4: 68 percent / H₂ / Lindlar catalyst / hexane / 1 h / 760 Torr

5: diisobutylaluminum hydride / benzene; hexane / 3 h / Ambient temperature

With bis-triphenylphosphine-palladium(II) chloride; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; Lindlar's catalyst; In hexane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00243a035

Reference yield:

(S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate (66774-80-9,111924-49-3) → 25-hydroxy-3-deoxy-2-oxavitamin D3 (113490-39-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 89 percent / Li₂CuCl₄ / tetrahydrofuran / 10 h / Ambient temperature

2: 82 percent / pyridinium dichromate (PDC), pyridinium trifluoroacetate (PTFA) / CH₂Cl₂ / 4.5 h / Ambient temperature

3: 1.) lithium diisopropylamide / 1.) THF, hexane, from -78 deg C to RT, 2h, 2.) THF, 0 deg C, 15 h

4: 81 percent / Et₃N, Pd(PPh₃)2Cl₂ / dimethylformamide / 4.5 h / 75 °C

5: 68 percent / H₂ / Lindlar catalyst / hexane / 1 h / 760 Torr

6: diisobutylaluminum hydride / benzene; hexane / 3 h / Ambient temperature

With bis-triphenylphosphine-palladium(II) chloride; dipyridinium dichromate; dilithium tetrachlorocuprate; hydrogen; pyridinium trifluroacetate; diisobutylaluminium hydride; triethylamine; lithium diisopropyl amide; Lindlar's catalyst; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00243a035

Reference yield:

de-A,B-25-cholesten-8β-ol (66774-82-1) → 25-hydroxy-3-deoxy-2-oxavitamin D3 (113490-39-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 82 percent / pyridinium dichromate (PDC), pyridinium trifluoroacetate (PTFA) / CH₂Cl₂ / 4.5 h / Ambient temperature

2: 1.) lithium diisopropylamide / 1.) THF, hexane, from -78 deg C to RT, 2h, 2.) THF, 0 deg C, 15 h

3: 81 percent / Et₃N, Pd(PPh₃)2Cl₂ / dimethylformamide / 4.5 h / 75 °C

4: 68 percent / H₂ / Lindlar catalyst / hexane / 1 h / 760 Torr

5: diisobutylaluminum hydride / benzene; hexane / 3 h / Ambient temperature

With bis-triphenylphosphine-palladium(II) chloride; dipyridinium dichromate; hydrogen; pyridinium trifluroacetate; diisobutylaluminium hydride; triethylamine; lithium diisopropyl amide; Lindlar's catalyst; In hexane; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00243a035

upstream raw materials:

2-nor-1,3-seco-25-dehydro-1-hydroxyvitamin D₃

pent-3-yn-1-ol

(S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate

de-A,B-25-cholesten-8β-ol

Refernces