Acetic acid (5S,5aS,6R,8aR,9R)-6-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-8-oxo-9-(3,4,5-trimethoxy-phenyl)-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl ester

Base Information

• Chemical Name: Acetic acid (5S,5aS,6R,8aR,9R)-6-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-8-oxo-9-(3,4,5-trimethoxy-phenyl)-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl ester
• CAS No.: 151697-38-0
• Molecular Formula: C₃₄H₄₂O₁₀
• Molecular Weight: 610.701

Synonyms:Acetic acid (5S,5aS,6R,8aR,9R)-6-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-8-oxo-9-(3,4,5-trimethoxy-phenyl)-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl ester

Chemical Property of Acetic acid (5S,5aS,6R,8aR,9R)-6-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-8-oxo-9-(3,4,5-trimethoxy-phenyl)-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of Acetic acid (5S,5aS,6R,8aR,9R)-6-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-8-oxo-9-(3,4,5-trimethoxy-phenyl)-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl ester

There total 4 articles about Acetic acid (5S,5aS,6R,8aR,9R)-6-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-8-oxo-9-(3,4,5-trimethoxy-phenyl)-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl ester 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: 80.5%

lead(IV) tetraacetate (546-67-8) + (5R,5aS,6R,8aR,9R)-6-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-8-oxo-9-(3,4,5-trimethoxy-phenyl)-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5-carboxylic acid (151697-37-9) → Acetic acid (5S,5aS,6R,8aR,9R)-6-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-8-oxo-9-(3,4,5-trimethoxy-phenyl)-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl ester (151697-38-0)

Guidance literature:

With acetic acid; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1039/c39930001200

Reference yield:

(5R,5aR,6R)-6-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-8-oxo-9-(3,4,5-trimethoxy-phenyl)-5,5a,6,8-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5-carboxylic acid (151697-36-8) → Acetic acid (5S,5aS,6R,8aR,9R)-6-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-8-oxo-9-(3,4,5-trimethoxy-phenyl)-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl ester (151697-38-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / H₂ / 10percent Pd/C / ethyl acetate / 40 h / 22 °C

2: 80.5 percent / acetic acid; tetrahydrofuran / 3 h / 20 °C

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; acetic acid; ethyl acetate;

DOI:10.1039/P19960000151

Reference yield:

C33H38O10 (151697-35-7) → Acetic acid (5S,5aS,6R,8aR,9R)-6-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-8-oxo-9-(3,4,5-trimethoxy-phenyl)-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl ester (151697-38-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / AcOH / 13 h / 49 °C

2: 71 percent / H₂ / 10percent Pd/C / ethyl acetate / 40 h / 22 °C

3: 80.5 percent / acetic acid; tetrahydrofuran / 3 h / 20 °C

With hydrogen; acetic acid; palladium on activated charcoal; In tetrahydrofuran; acetic acid; ethyl acetate;

DOI:10.1039/P19960000151

upstream raw materials:

lead(IV) tetraacetate

(5R,5aS,6R,8aR,9R)-6-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-8-oxo-9-(3,4,5-trimethoxy-phenyl)-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5-carboxylic acid

6,7-methylenedioxy-1-(3',4',5'-trimethoxyphenyl)-2-benzopyran-3-one

C₃₃H₃₈O₁₀

Downstream raw materials:

(5R,6R,7R,8R)-methyl 8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydronaphtho[2,3-d][1,3]dioxole-6-carboxylate

(-)-Methyl epipodophyllate

(5R,6R,7S,8S)-7-Formyl-8-hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester

(5R,6R,7S,8R)-7-Formyl-8-hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester

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