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

Base Information

Chemical Name:7α-acetoxy-1α-benzyloxy-12α,13α-epoxy-4α,8β,13β-trimethyl-19-norpodocarpane-2,14-dione
CAS No.:204130-79-0
Molecular Formula:C₂₇H₃₄O₆
Molecular Weight:454.563
Hs Code.:

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

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

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

There total 7 articles about 7α-acetoxy-1α-benzyloxy-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: 94.0%

: 108-24-7
acetic anhydride

: 204130-85-8
1α-benzyloxy-12α,13α-epoxy-7α-hydroxy-4α,8β,13β-trimethyl-19-norpodocarpane-2,14-dione

: 204130-79-0
7α-acetoxy-1α-benzyloxy-12α,13α-epoxy-4α,8β,13β-trimethyl-19-norpodocarpane-2,14-dione

Guidance literature:: With dmap; In dichloromethane; Ambient temperature;
DOI:10.1021/jo9718962

Reference yield:

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

: 204130-79-0
7α-acetoxy-1α-benzyloxy-12α,13α-epoxy-4α,8β,13β-trimethyl-19-norpodocarpane-2,14-dione

Guidance literature:: Multi-step reaction with 5 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

4.1: 92 percent / BF₃*Et₂O / CH₂Cl₂ / 0 - 10 °C

5.1: 94 percent / DMAP / CH₂Cl₂ / 20 °C

With dmap; boron trifluoride diethyl etherate; hydrogen; sodium hydride; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; 1.1: Deacetylation / 2.1: Catalytic hydrogenation / 3.1: Deprotonation / 3.2: Benzylation / 4.1: Desilylation / 5.1: Acetylation;
DOI:10.1021/jo000877g

Reference yield:

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

: 204130-79-0
7α-acetoxy-1α-benzyloxy-12α,13α-epoxy-4α,8β,13β-trimethyl-19-norpodocarpane-2,14-dione

Guidance literature:: Multi-step reaction with 4 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

3.1: 92 percent / BF₃*Et₂O / CH₂Cl₂ / 0 - 10 °C

4.1: 94 percent / DMAP / CH₂Cl₂ / 20 °C

With dmap; boron trifluoride diethyl etherate; hydrogen; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; 1.1: Catalytic hydrogenation / 2.1: Deprotonation / 2.2: Benzylation / 3.1: Desilylation / 4.1: Acetylation;
DOI:10.1021/jo000877g