Silvestrol aglycone

Base Information

• Chemical Name: Silvestrol aglycone
• CAS No.: 960365-65-5
• Molecular Formula: C27H26O8
• Molecular Weight: 478.499
• Mol file: 960365-65-5.mol

Synonyms:CS-0542;Silvestrol aglycone;

Chemical Property of Silvestrol aglycone

Chemical Property:

• Melting Point: 127-129℃
• PSA: 114.68000
• Density: 1.408
• LogP: 2.83240

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Silvestrol aglycone

There total 16 articles about Silvestrol aglycone 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: 95.0%

C34H32O8 (1112993-16-4) → (1R,2R,3S,3aR,8bS)-methyl 1,6,8b-trihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2-carboxylate (960365-65-5)

Guidance literature:

With 20% Pd/C; hydrogen; In ethanol; for 3h;

DOI:10.1021/np300376f

Reference yield:

C29H30O9 (960365-75-7) → (1R,2R,3S,3aR,8bS)-methyl 1,6,8b-trihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2-carboxylate (960365-65-5)

Guidance literature:

With trimethylsilyl bromide; In dichloromethane; at -78 ℃; for 1h;

DOI:10.1002/anie.200702707

Reference yield:

7-(benzyloxy)-3-hydroxy-5-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one (874202-33-2) → (1R,2R,3S,3aR,8bS)-methyl 1,6,8b-trihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2-carboxylate (960365-65-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: chloroform; 2,2,2-trifluoroethanol / 15 h / -5 °C / Inert atmosphere; UV-irradiation

2.1: sodium methylate / methanol / 0.67 h / Reflux

2.2: 19 h / Inert atmosphere

3.1: 5 μm Phenomenex Lux Cellulose-1 semipreparative column / acetonitrile; water / Resolution of racemate

4.1: hydrogen; 20% Pd/C / ethanol / 3 h

With 20% Pd/C; hydrogen; sodium methylate; In methanol; ethanol; chloroform; 2,2,2-trifluoroethanol; water; acetonitrile;

DOI:10.1021/np300376f

upstream raw materials:

C₂₉H₃₀O₉

C₃₄H₃₂O₈

7-(benzyloxy)-3-hydroxy-5-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

Methyl cinnamate

Downstream raw materials:

C₄₆H₆₆O₁₃Si₂

aglafoline

(1R,2R,3S,3aR,8bS)-methyl 1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-6-(trifluoromethylsulfonyloxy)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxylate

(1R,2R,3S,3aR,8bS)-methyl 6-acetyl-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2-carboxylate