(Z)-3-Methoxy-5,24,25-tris-(4-methoxy-benzyloxy)-tricyclo[20.2.2.0^2,7]hexacosa-1⁽²⁵⁾,2⁽⁷⁾,3,5,11,22⁽²⁶⁾,23-heptaene

Base Information

• Chemical Name: (Z)-3-Methoxy-5,24,25-tris-(4-methoxy-benzyloxy)-tricyclo[20.2.2.0^2,7]hexacosa-1⁽²⁵⁾,2⁽⁷⁾,3,5,11,22⁽²⁶⁾,23-heptaene
• CAS No.: 444119-97-5
• Molecular Formula: C₅₁H₆₀O₇
• Molecular Weight: 785.033
• Mol file: 444119-97-5.mol

Synonyms:(Z)-3-Methoxy-5,24,25-tris-(4-methoxy-benzyloxy)-tricyclo[20.2.2.0^2,7]hexacosa-1⁽²⁵⁾,2⁽⁷⁾,3,5,11,22⁽²⁶⁾,23-heptaene

Chemical Property of (Z)-3-Methoxy-5,24,25-tris-(4-methoxy-benzyloxy)-tricyclo[20.2.2.0^2,7]hexacosa-1⁽²⁵⁾,2⁽⁷⁾,3,5,11,22⁽²⁶⁾,23-heptaene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-3-Methoxy-5,24,25-tris-(4-methoxy-benzyloxy)-tricyclo[20.2.2.0^2,7]hexacosa-1⁽²⁵⁾,2⁽⁷⁾,3,5,11,22⁽²⁶⁾,23-heptaene

There total 28 articles about (Z)-3-Methoxy-5,24,25-tris-(4-methoxy-benzyloxy)-tricyclo[20.2.2.0^2,7]hexacosa-1⁽²⁵⁾,2⁽⁷⁾,3,5,11,22⁽²⁶⁾,23-heptaene 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: 96.0%

3-methoxy-5,24,25-tris-(4-methoxy-benzyloxy)-tricyclo[20.2.2.02,7]hexacosa-1(25),2(7),3,5,22(26),23-hexaen-11-yne (444119-72-6) → (Z)-3-Methoxy-5,24,25-tris-(4-methoxy-benzyloxy)-tricyclo[20.2.2.02,7]hexacosa-1(25),2(7),3,5,11,22(26),23-heptaene (444119-97-5)

Guidance literature:

With quinoline; hydrogen; Lindlar's catalyst; In ethyl acetate; for 6h; under 760 Torr;

DOI:10.1002/1521-3765(20020415)8:8<1850::AID-CHEM1850>3.0.CO;2-Q

Reference yield:

5-bromo-4-hydroxy-3-methoxybenzaldehyde (2973-76-4) → (Z)-3-Methoxy-5,24,25-tris-(4-methoxy-benzyloxy)-tricyclo[20.2.2.02,7]hexacosa-1(25),2(7),3,5,11,22(26),23-heptaene (444119-97-5)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 97 percent / K₂CO₃ / dimethylformamide / 24 h / 20 °C

2.1: 70 percent / 3-chloroperbenzoic acid / CH₂Cl₂ / 16 h / Heating

3.1: 89 percent / dimethylformamide / 12 h / Heating

4.1: 82 percent / K₂CO₃; n-Bu₄NI / dimethylformamide / 12 h / 80 °C

5.1: 98 percent / aq. LiOH / methanol / 72 h / Heating

6.1: 80 percent / PPh₃; (iPr)2NEt; CCl₄ / pyridine; acetonitrile / 16 h / 80 °C

7.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 3 h / Heating

7.2: 84 percent / tetrahydrofuran / 48 h / Heating

8.1: methyl triflate / CH₂Cl₂ / 2 h / -10 - 0 °C

8.2: NaBH₄ / methanol; tetrahydrofuran; CH₂Cl₂ / 3 h / 20 °C

8.3: 70 percent / aq. oxalic acid / tetrahydrofuran / 12 h

9.1: 82 percent / tetrahydrofuran / 1 h / 0 °C

10.1: 94 percent / pyridine / CH₂Cl₂ / 13 h / -20 - 20 °C

11.1: 97 percent / n-Bu₃SnH; AIBN / toluene / 12 h / 75 °C

12.1: 99 percent / TBAF*3H₂O / tetrahydrofuran / 2 h / 20 °C

13.1: methanesulfonic anhydride; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

13.2: 73 percent / LiBr / tetrahydrofuran / 2 h / 60 °C

14.1: 65 percent / Li₂CuCl₄ / tetrahydrofuran / 1 h / -20 °C

15.1: [(PCy₃)2Cl₂Ru=(3-phenylindenylidene)] / CH₂Cl₂ / 4 h / Heating

With pyridine; tetrachloromethane; lithium hydroxide; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; potassium carbonate; magnesium; ethylene dibromide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; methyl trifluoromethanesulfonate; Methanesulfonic anhydride; dilithium tetrachlorocuprate; [(PCy₃)2Cl₂Ru=(3-phenylindenylidene)]; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 2.1: Baeyer-Villiger oxidation;

DOI:10.1002/1521-3765(20020415)8:8<1850::AID-CHEM1850>3.0.CO;2-Q

Reference yield:

3,5-dihydroxy-4-bromobenzoic acid (16534-12-6) → (Z)-3-Methoxy-5,24,25-tris-(4-methoxy-benzyloxy)-tricyclo[20.2.2.02,7]hexacosa-1(25),2(7),3,5,11,22(26),23-heptaene (444119-97-5)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 96 percent / SOCl₂ / 2 h / Heating

2.1: 84 percent / K₂CO₃; nBu₄NI / dimethylformamide / 12 h / 80 °C

3.1: 98 percent / LiBH₄ / tetrahydrofuran; methanol / 3 h / Heating

4.1: 82 percent / imidazole / dimethylformamide / 12 h / 20 °C

5.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 3 h / Heating

5.2: 84 percent / tetrahydrofuran / 48 h / Heating

6.1: methyl triflate / CH₂Cl₂ / 2 h / -10 - 0 °C

6.2: NaBH₄ / methanol; tetrahydrofuran; CH₂Cl₂ / 3 h / 20 °C

6.3: 70 percent / aq. oxalic acid / tetrahydrofuran / 12 h

7.1: 82 percent / tetrahydrofuran / 1 h / 0 °C

8.1: 94 percent / pyridine / CH₂Cl₂ / 13 h / -20 - 20 °C

9.1: 97 percent / n-Bu₃SnH; AIBN / toluene / 12 h / 75 °C

10.1: 99 percent / TBAF*3H₂O / tetrahydrofuran / 2 h / 20 °C

11.1: methanesulfonic anhydride; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

11.2: 73 percent / LiBr / tetrahydrofuran / 2 h / 60 °C

12.1: 65 percent / Li₂CuCl₄ / tetrahydrofuran / 1 h / -20 °C

13.1: [(PCy₃)2Cl₂Ru=(3-phenylindenylidene)] / CH₂Cl₂ / 4 h / Heating

With pyridine; 1H-imidazole; lithium borohydride; thionyl chloride; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; potassium carbonate; magnesium; ethylene dibromide; triethylamine; methyl trifluoromethanesulfonate; Methanesulfonic anhydride; dilithium tetrachlorocuprate; [(PCy₃)2Cl₂Ru=(3-phenylindenylidene)]; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1002/1521-3765(20020415)8:8<1850::AID-CHEM1850>3.0.CO;2-Q

upstream raw materials:

3-methoxy-5,24,25-tris-(4-methoxy-benzyloxy)-tricyclo[20.2.2.0^2,7]hexacosa-1⁽²⁵⁾,2⁽⁷⁾,3,5,22⁽²⁶⁾,23-hexaen-11-yne

2-methoxy-4,2',6'-tris-(4-methoxybenzyloxy)-6-pent-4-ynyl-4'-undec-10-enyl-biphenyl

5-bromo-4-hydroxy-3-methoxybenzaldehyde

3,5-dihydroxy-4-bromobenzoic acid