1α-benzyloxy-7α-(tert-butyldimethylsiloxy)-12α,13α-epoxy-4α,8β,13β-trimethyl-19-norpodocarpane-2,14-dione

Base Information

• Chemical Name: 1α-benzyloxy-7α-(tert-butyldimethylsiloxy)-12α,13α-epoxy-4α,8β,13β-trimethyl-19-norpodocarpane-2,14-dione
• CAS No.: 204130-78-9
• Molecular Formula: C₃₁H₄₆O₅Si
• Molecular Weight: 526.789
• Mol file: 204130-78-9.mol

Synonyms:1α-benzyloxy-7α-(tert-butyldimethylsiloxy)-12α,13α-epoxy-4α,8β,13β-trimethyl-19-norpodocarpane-2,14-dione

Chemical Property of 1α-benzyloxy-7α-(tert-butyldimethylsiloxy)-12α,13α-epoxy-4α,8β,13β-trimethyl-19-norpodocarpane-2,14-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1α-benzyloxy-7α-(tert-butyldimethylsiloxy)-12α,13α-epoxy-4α,8β,13β-trimethyl-19-norpodocarpane-2,14-dione

There total 3 articles about 1α-benzyloxy-7α-(tert-butyldimethylsiloxy)-12α,13α-epoxy-4α,8β,13β-trimethyl-19-norpodocarpane-2,14-dione 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: 85.0%

benzyl bromide (100-39-0) + 7α-(tert-butyldimethylsiloxy)-12α,13α-epoxy-1α-hydroxy-4α,8β,13β-trimethyl-19-norpodocarpane-2,14-dione (204130-77-8) → 1α-benzyloxy-7α-(tert-butyldimethylsiloxy)-12α,13α-epoxy-4α,8β,13β-trimethyl-19-norpodocarpane-2,14-dione (204130-78-9)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/jo9718962

Reference yield:

1α-acetoxy-7α-(tert-butyldimethylsiloxy)-12α,13α-epoxy-4,8β,13β-trimethyl-19-norpodocarp-3-ene-2,14-dione (204130-76-7) → 1α-benzyloxy-7α-(tert-butyldimethylsiloxy)-12α,13α-epoxy-4α,8β,13β-trimethyl-19-norpodocarpane-2,14-dione (204130-78-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 87 percent / K₂CO₃ / methanol / 4 h / 20 °C

2.1: 99 percent / H₂ / Pd/C / ethanol / 4 h / 20 °C

3.1: NaH / tetrahydrofuran / 1 h / 0 °C

3.2: 85 percent / TBAI / tetrahydrofuran / 0 - 20 °C

With hydrogen; sodium hydride; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; 1.1: Deacetylation / 2.1: Catalytic hydrogenation / 3.1: Deprotonation / 3.2: Benzylation;

DOI:10.1021/jo000877g

Reference yield:

7α-(tert-butyldimethylsiloxy)-12α,13α-epoxy-1α-hydroxy-4,8β,13β-trimethyl-19-norpodocarp-3-ene-2,14-dione (204130-84-7) → 1α-benzyloxy-7α-(tert-butyldimethylsiloxy)-12α,13α-epoxy-4α,8β,13β-trimethyl-19-norpodocarpane-2,14-dione (204130-78-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 99 percent / H₂ / Pd/C / ethanol / 4 h / 20 °C

2.1: NaH / tetrahydrofuran / 1 h / 0 °C

2.2: 85 percent / TBAI / tetrahydrofuran / 0 - 20 °C

With hydrogen; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; ethanol; 1.1: Catalytic hydrogenation / 2.1: Deprotonation / 2.2: Benzylation;

DOI:10.1021/jo000877g

upstream raw materials:

benzyl bromide

7α-(tert-butyldimethylsiloxy)-12α,13α-epoxy-1α-hydroxy-4α,8β,13β-trimethyl-19-norpodocarpane-2,14-dione

7α-(tert-butyldimethylsiloxy)-12α,13α-epoxy-1α-hydroxy-4,8β,13β-trimethyl-19-norpodocarp-3-ene-2,14-dione

1α-acetoxy-7α-(tert-butyldimethylsiloxy)-12α,13α-epoxy-4,8β,13β-trimethyl-19-norpodocarp-3-ene-2,14-dione

Downstream raw materials:

1α-benzyloxy-12α,13α-epoxy-7α-hydroxy-4α,8β,13β-trimethyl-19-norpodocarpane-2,14-dione

1α-benzyloxy-12α,13α-epoxy-14β-hydroxypicrasane-2,16-dione

7α-acetoxy-1α-benzyloxy-12α,13α-epoxy-4α,8β,13β-trimethyl-19-norpodocarpane-2,14-dione