[4,6-dihydroxy-2-methoxymethoxy-3-(3-methyl-but-2-enyl)-phenyl]-[4,6-dihydroxy-3-methoxy-2-(3-methyl-but-2-enyl)-phenyl]-methanone

Base Information

• Chemical Name: [4,6-dihydroxy-2-methoxymethoxy-3-(3-methyl-but-2-enyl)-phenyl]-[4,6-dihydroxy-3-methoxy-2-(3-methyl-but-2-enyl)-phenyl]-methanone
• CAS No.: 426820-49-7
• Molecular Formula: C₂₆H₃₂O₈
• Molecular Weight: 472.535
• Mol file: 426820-49-7.mol

Synonyms:[4,6-dihydroxy-2-methoxymethoxy-3-(3-methyl-but-2-enyl)-phenyl]-[4,6-dihydroxy-3-methoxy-2-(3-methyl-but-2-enyl)-phenyl]-methanone

Chemical Property of [4,6-dihydroxy-2-methoxymethoxy-3-(3-methyl-but-2-enyl)-phenyl]-[4,6-dihydroxy-3-methoxy-2-(3-methyl-but-2-enyl)-phenyl]-methanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of [4,6-dihydroxy-2-methoxymethoxy-3-(3-methyl-but-2-enyl)-phenyl]-[4,6-dihydroxy-3-methoxy-2-(3-methyl-but-2-enyl)-phenyl]-methanone

There total 23 articles about [4,6-dihydroxy-2-methoxymethoxy-3-(3-methyl-but-2-enyl)-phenyl]-[4,6-dihydroxy-3-methoxy-2-(3-methyl-but-2-enyl)-phenyl]-methanone 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: 63.0%

[4,6-bis-benzyloxy-2-methoxymethoxy-3-(3-methyl-but-2-enyl)-phenyl]-[4,6-bis-benzyloxy-3-methoxy-2-(3-methyl-but-2-enyl)-phenyl]-methanone (426820-55-5) → [4,6-dihydroxy-2-methoxymethoxy-3-(3-methyl-but-2-enyl)-phenyl]-[4,6-dihydroxy-3-methoxy-2-(3-methyl-but-2-enyl)-phenyl]-methanone (426820-49-7)

Guidance literature:

With ammonium formate; palladium on activated charcoal; In acetone; at 20 ℃;

DOI:10.1016/S0040-4039(01)02137-2

Reference yield:

3,5-dihydroxyphenol (108-73-6) → [4,6-dihydroxy-2-methoxymethoxy-3-(3-methyl-but-2-enyl)-phenyl]-[4,6-dihydroxy-3-methoxy-2-(3-methyl-but-2-enyl)-phenyl]-methanone (426820-49-7)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 96 percent / NaH / dimethylformamide / 20 °C

2.1: nBuLi

2.2: 89 percent / tetrahydrofuran / 0 °C

3.1: nBuLi

3.2: 95 percent / tetrahydrofuran / 0 °C

4.1: 100 percent / CSA; MeOH / 60 °C

5.1: 100 percent / DMAP; Et₃N / dimethylformamide / 20 °C

6.1: 78 percent / DIBAL-H / toluene / -78 °C

7.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C

8.1: 65 percent / NaH / CH₂Cl₂ / 20 °C

9.1: 100 percent / TBAF / tetrahydrofuran / 0 °C

10.1: 98 percent / K₂CO₃ / dimethylformamide / 20 °C

11.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C

12.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C

13.1: 63 percent / HCO₂NH₄ / Pd/C / acetone / 20 °C

With methanol; dmap; n-butyllithium; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sec.-butyllithium; ammonium formate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1016/S0040-4039(01)02137-2

Reference yield:

2,4-bis(benzyloxy)phenol (6195-80-8) → [4,6-dihydroxy-2-methoxymethoxy-3-(3-methyl-but-2-enyl)-phenyl]-[4,6-dihydroxy-3-methoxy-2-(3-methyl-but-2-enyl)-phenyl]-methanone (426820-49-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 84 percent / Br₂ / CHCl₃ / 20 °C

2: 80 percent / K₂CO₃ / dimethylformamide / 20 °C

3: 73 percent / 160 °C

4: 87 percent / K₂CO₃ / dimethylformamide / 20 °C

5: 95 percent / OsO₄; NaIO₄ / H₂O; diethyl ether / 20 °C

6: 72 percent / nBuLi / tetrahydrofuran / 0 °C

7: 49 percent / sBuLi / tetrahydrofuran / -78 °C

8: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C

9: 63 percent / HCO₂NH₄ / Pd/C / acetone / 20 °C

With sodium periodate; osmium(VIII) oxide; n-butyllithium; bromine; sec.-butyllithium; ammonium formate; potassium carbonate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; chloroform; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; 3: Claisen rearrangement / 5: Lemieux-Johnson oxidation / 6: Wittig reaction;

DOI:10.1016/S0040-4039(01)02137-2

upstream raw materials:

[4,6-bis-benzyloxy-2-methoxymethoxy-3-(3-methyl-but-2-enyl)-phenyl]-[4,6-bis-benzyloxy-3-methoxy-2-(3-methyl-but-2-enyl)-phenyl]-methanone

3,5-dihydroxyphenol

2,4-bis(benzyloxy)phenol

2,4-dibenzyloxybenzaldehyde

Downstream raw materials:

α-mangostin