combretastatin D-2 benzyl ether

Base Information

• Chemical Name: combretastatin D-2 benzyl ether
• CAS No.: 202645-48-5
• Molecular Formula: C₂₅H₂₂O₄
• Molecular Weight: 386.447
• Mol file: 202645-48-5.mol

Synonyms:combretastatin D-2 benzyl ether

Chemical Property of combretastatin D-2 benzyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of combretastatin D-2 benzyl ether

There total 17 articles about combretastatin D-2 benzyl ether 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: 92.0%

(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) → combretastatin D-2 benzyl ether (202645-48-5)

Guidance literature:

With 1H-imidazole; tri-iodoimidazole; triphenylphosphine; In 1,1,2,2-tetrachloroethylene; at 140 ℃; for 0.5h;

DOI:10.1002/(SICI)1521-3765(199801)4:1<33::AID-CHEM33>3.0.CO;2-8

Reference yield: 10.0%

3'-(4'''-bromophenyl)-2'Z-propenyl 3-(3''-hydroxy-4''-benzyloxyphenyl)propanoate (1146133-44-9) → combretastatin D-2 benzyl ether (202645-48-5)

Guidance literature:

With copper(I) bromide dimethylsulfide complex; potassium carbonate; In pyridine; Inert atmosphere; Reflux;

DOI:10.1021/np800635h

Reference yield:

4-benzyloxy-3-hydroxy-benzaldehyde (4049-39-2) → combretastatin D-2 benzyl ether (202645-48-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 93 percent / benzene / 2 h / 25 °C

2: 97 percent / H₂ / 5percent Pd/C / benzene / 5 h / 25 °C

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

4: 87 percent / K₃Fe(CN)6, K₂CO₃, (DHQD)2PHAL, K₂Os₂(OH)4, CH₃SO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 12 h / 0 °C

5: 97 percent / imidazole / dimethylformamide / 3 h / 25 °C

6: 94 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / 0 - 25 °C

7: 90 percent / DIBAL-H / CH₂Cl₂; cyclohexane / 0.17 h / -78 °C

8: 81 percent / DEAD, PPh₃ / toluene / 14 h / 45 °C

9: 94 percent / TBAF / tetrahydrofuran / 3 h / 25 °C

10: 92 percent / PPh₃, imidazole, triiodoimidazole / tetrachloroethene / 0.5 h / 140 °C

With 1H-imidazole; potassium osmate; lithium hydroxide; copper(I) bromide dimethylsulfide complex; methanesulfonamide; tri-iodoimidazole; 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; pyridine; methanol; 1,1,2,2-tetrachloroethylene; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; benzene;

DOI:10.1002/(SICI)1521-3765(199801)4:1<33::AID-CHEM33>3.0.CO;2-8

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-2