C₂₅H₂₂O₅

Base Information

• Chemical Name: C₂₅H₂₂O₅
• CAS No.: 172919-12-9
• Molecular Formula: C₂₅H₂₂O₅
• Molecular Weight: 402.447
• Mol file: 172919-12-9.mol

Synonyms:C₂₅H₂₂O₅

Chemical Property of C₂₅H₂₂O₅

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₂₅H₂₂O₅

There total 15 articles about C₂₅H₂₂O₅ 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: 87.0%

(13R,14R)-4-benzyloxy-13,14-dihydroxy-2,11-dioxatricyclo[13.2.2.13,7]eicosa-1(18),3,5,7(20),1(19),16-hexaen-10-one (172919-05-0) → C25H22O5 (172919-12-9)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In N,N-dimethyl-formamide; at 145 ℃; for 0.666667h;

DOI:10.1016/0040-4039(95)01987-S

Reference yield:

4-benzyloxy-3-hydroxy-benzaldehyde (4049-39-2) → C25H22O5 (172919-12-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 93 percent / benzene / Ambient temperature

2: 97 percent / H₂ / 5 percent Pd/C / benzene / 5 h / Ambient temperature

3: 78 percent / CuBr*Me₂S, K₂CO₃, pyridine / 6 h / 140 °C

4: 87 percent / K₃Fe(CN)6, K₂CO₃, K₂OsO₂(OH)4, (DHQD)2PHAL / 2-methyl-propan-2-ol; H₂O / 12 h / 0 °C

5: 97 percent / imidazole / dimethylformamide / 3 h / Ambient temperature

6: 1.) LiOH, 2.) DIBAL / 1.) THF/MeOH, 0 deg C -> RT, 2 h, 2.) CH₂Cl₂, -78 deg C, 10 min

7: 81 percent / DEAD, Ph₃P / toluene / 6 h / 45 °C

8: 94 percent / TBAF / tetrahydrofuran / 3 h / Ambient temperature

9: 87 percent / DEAD, Ph₃P / dimethylformamide / 0.67 h / 145 °C

With pyridine; 1H-imidazole; lithium hydroxide; potassium dioxotetrahydroxoosmate(VI); copper(I) bromide dimethylsulfide complex; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; triphenylphosphine; potassium hexacyanoferrate(III); diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; benzene;

DOI:10.1016/0040-4039(95)01987-S

Reference yield:

benzyl bromide (100-39-0) → C25H22O5 (172919-12-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) K₂CO₃ / 1.) DMF, 60 deg C, 4 h, 2.) DMF, RT, 12 h

2: 93 percent / benzene / Ambient temperature

3: 97 percent / H₂ / 5 percent Pd/C / benzene / 5 h / Ambient temperature

4: 78 percent / CuBr*Me₂S, K₂CO₃, pyridine / 6 h / 140 °C

5: 87 percent / K₃Fe(CN)6, K₂CO₃, K₂OsO₂(OH)4, (DHQD)2PHAL / 2-methyl-propan-2-ol; H₂O / 12 h / 0 °C

6: 97 percent / imidazole / dimethylformamide / 3 h / Ambient temperature

7: 1.) LiOH, 2.) DIBAL / 1.) THF/MeOH, 0 deg C -> RT, 2 h, 2.) CH₂Cl₂, -78 deg C, 10 min

8: 81 percent / DEAD, Ph₃P / toluene / 6 h / 45 °C

9: 94 percent / TBAF / tetrahydrofuran / 3 h / Ambient temperature

10: 87 percent / DEAD, Ph₃P / dimethylformamide / 0.67 h / 145 °C

With pyridine; 1H-imidazole; lithium hydroxide; potassium dioxotetrahydroxoosmate(VI); copper(I) bromide dimethylsulfide complex; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; triphenylphosphine; potassium hexacyanoferrate(III); diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; benzene;

DOI:10.1016/0040-4039(95)01987-S

upstream raw materials:

(13R,14R)-4-benzyloxy-13,14-dihydroxy-2,11-dioxatricyclo[13.2.2.1^3,7]eicosa-1⁽¹⁸⁾,3,5,7⁽²⁰⁾,1⁽¹⁹⁾,16-hexaen-10-one

4-benzyloxy-3-hydroxy-benzaldehyde

ethyl (E)-3-(4-bromophenyl)-2-propenoate

(2E)-3-(4-bromophenyl)prop-2-en-1-ol

Downstream raw materials:

combretastatin D-1

Refernces