5-benzyloxymethyl-13β,14β-dihdyroxymethyl-5,9-dimethyl-21-isopropyltetracyclo[10.2.2.0^1,0.0^4.9]hexadec-15-ene

Base Information

• Chemical Name: 5-benzyloxymethyl-13β,14β-dihdyroxymethyl-5,9-dimethyl-21-isopropyltetracyclo[10.2.2.0^1,0.0^4.9]hexadec-15-ene
• CAS No.: 185819-56-1
• Molecular Formula: C₃₁H₄₆O₃
• Molecular Weight: 466.704

Synonyms:5-benzyloxymethyl-13β,14β-dihdyroxymethyl-5,9-dimethyl-21-isopropyltetracyclo[10.2.2.0^1,0.0^4.9]hexadec-15-ene

Chemical Property of 5-benzyloxymethyl-13β,14β-dihdyroxymethyl-5,9-dimethyl-21-isopropyltetracyclo[10.2.2.0^1,0.0^4.9]hexadec-15-ene

Chemical Property:

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Technology Process of 5-benzyloxymethyl-13β,14β-dihdyroxymethyl-5,9-dimethyl-21-isopropyltetracyclo[10.2.2.0^1,0.0^4.9]hexadec-15-ene

There total 5 articles about 5-benzyloxymethyl-13β,14β-dihdyroxymethyl-5,9-dimethyl-21-isopropyltetracyclo[10.2.2.0^1,0.0^4.9]hexadec-15-ene 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: 80.0%

13α,19α-5-benzyloxymethyl-5,9-dimethyl-21-isopropyl-16-phenyl-15,17-dioxapentacyclo[10.7.2.01,10.04,9.013,19]heneicos-20-ene (185819-54-9) → 5-benzyloxymethyl-13β,14β-dihdyroxymethyl-5,9-dimethyl-21-isopropyltetracyclo[10.2.2.01,0.04.9]hexadec-15-ene (185819-56-1)

Guidance literature:

With pyridinium p-toluenesulfonate; In methanol; at 40 ℃; for 3h;

DOI:10.1023/A:1013144431609

Reference yield: 50.0%

13α,19α-5-benzyloxymethyl-5,9-dimethyl-21-isopropyl-16-phenyl-15,17-dioxapentacyclo[10.7.2.01,10.04,9.013,19]heneicos-20-ene (185819-54-9) → 5-benzyloxymethyl-13β,14β-dihdyroxymethyl-5,9-dimethyl-21-isopropyltetracyclo[10.2.2.01,0.04.9]hexadec-15-ene (185819-56-1) + 16α,17α-5-benzyloxymethyl-17-hydroxyemthyl-5,9-dimethyl-13-isopropyl-14-oxapentacyclo[11.4.1.01,10.04.9.012,17]octadecane

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 1h;

DOI:10.1023/A:1013144431609

Reference yield:

5,9-dimethyl-16-isopropyl-5,13β,14β-trihydroxymethyltetracyclo[10.2.2.01,10.04,9]hexadec-15-ene (22343-51-7) → 5-benzyloxymethyl-13β,14β-dihdyroxymethyl-5,9-dimethyl-21-isopropyltetracyclo[10.2.2.01,0.04.9]hexadec-15-ene (185819-56-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / p-toluenesulfonic acid / CH₂Cl₂ / 1 h / 20 °C

2: 86 percent / NaOH; tetrabutylammonium hydrogen sulfate / CH₂Cl₂ / 5 h / 45 - 50 °C

3: 80 percent / pyridinium p-toluenesulfonate / methanol / 3 h / 40 °C

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; In methanol; dichloromethane;

DOI:10.1023/A:1013144431609

upstream raw materials:

13α,19α-5-benzyloxymethyl-5,9-dimethyl-21-isopropyl-16-phenyl-15,17-dioxapentacyclo[10.7.2.0^1,10.0^4,9.0^13,19]heneicos-20-ene

5,9-dimethyl-16-isopropyl-5,13β,14β-trihydroxymethyltetracyclo[10.2.2.0^1,10.0^4,9]hexadec-15-ene

13α,19α-5-hydroxymethyl-5,9-dimethyl-21-isopropyl-16-phenyl-15,17-dioxapentacyclo[10.7.2.0^1,10.0^4,9.0^13,19]heneicos-20-ene

maleopimaric acid

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