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

Base Information

• Chemical Name: 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
• CAS No.: 185819-53-8
• Molecular Formula: C₃₁H₄₄O₃
• Molecular Weight: 464.689

Synonyms: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

Chemical Property of 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

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Technology Process of 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

There total 1 articles about 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 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: 70.0%

benzaldehyde dimethyl acetal (1125-88-8) + 5,9-dimethyl-16-isopropyl-5,13β,14β-trihydroxymethyltetracyclo[10.2.2.01,10.04,9]hexadec-15-ene (22343-51-7) → 13α,19α-5-hydroxymethyl-5,9-dimethyl-21-isopropyl-16-phenyl-15,17-dioxapentacyclo[10.7.2.01,10.04,9.013,19]heneicos-20-ene (185819-53-8)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1023/A:1013144431609

Reference yield: 86.0%

benzyl chloride (100-44-7) + 13α,19α-5-hydroxymethyl-5,9-dimethyl-21-isopropyl-16-phenyl-15,17-dioxapentacyclo[10.7.2.01,10.04,9.013,19]heneicos-20-ene (185819-53-8) → 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)

Guidance literature:

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane; at 45 - 50 ℃; for 5h;

DOI:10.1023/A:1013144431609

Reference yield:

13α,19α-5-hydroxymethyl-5,9-dimethyl-21-isopropyl-16-phenyl-15,17-dioxapentacyclo[10.7.2.01,10.04,9.013,19]heneicos-20-ene (185819-53-8) → 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 2 steps

1: 86 percent / NaOH; tetrabutylammonium hydrogen sulfate / CH₂Cl₂ / 5 h / 45 - 50 °C

2: 80 percent / pyridinium p-toluenesulfonate / methanol / 3 h / 40 °C

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

DOI:10.1023/A:1013144431609

upstream raw materials:

benzaldehyde dimethyl acetal

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

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

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