(1S,3S,5S)-1,7-bis(4-hydroxyphenyl)-1,5-epoxy-3-hydroxyheptane

Base Information

• Chemical Name: (1S,3S,5S)-1,7-bis(4-hydroxyphenyl)-1,5-epoxy-3-hydroxyheptane
• CAS No.: 1415609-84-5
• Molecular Formula: C₁₉H₂₂O₄
• Molecular Weight: 314.381
• Mol file: 1415609-84-5.mol

Synonyms:(1S,3S,5S)-1,7-bis(4-hydroxyphenyl)-1,5-epoxy-3-hydroxyheptane

Chemical Property of (1S,3S,5S)-1,7-bis(4-hydroxyphenyl)-1,5-epoxy-3-hydroxyheptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3S,5S)-1,7-bis(4-hydroxyphenyl)-1,5-epoxy-3-hydroxyheptane

There total 11 articles about (1S,3S,5S)-1,7-bis(4-hydroxyphenyl)-1,5-epoxy-3-hydroxyheptane 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: 86.0%

(2S,4S,6S)-2-(4-hydroxyphenethyl)-6-(4-hydroxyphenyl)tetrahydro-2H-pyran-4-yl 4-nitrobenzoate → (1S,3S,5S)-1,7-bis(4-hydroxyphenyl)-1,5-epoxy-3-hydroxyheptane (1415609-84-5)

Guidance literature:

With methanol; potassium carbonate; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tetlet.2016.06.102

Reference yield:

3-(4-hydroxy-phenyl)-propionic acid ethyl ester (23795-02-0) → (1S,3S,5S)-1,7-bis(4-hydroxyphenyl)-1,5-epoxy-3-hydroxyheptane (1415609-84-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

2.1: dmap; triethylamine / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 20 °C / Inert atmosphere

4.1: trifluoroacetic acid / dichloromethane / 4 h / Inert atmosphere; Reflux; Molecular sieve

4.2: 0.5 h / 20 °C / Inert atmosphere; Molecular sieve

4.3: 72 h / -78 - -20 °C / Inert atmosphere; Molecular sieve

5.1: trimethylsilyl acetate; acetic acid; boron trifluoride diethyl etherate / dichloromethane / 0 - 20 °C / Inert atmosphere

6.1: potassium carbonate; methanol / 1 h / 20 °C / Inert atmosphere

7.1: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 20 °C / Inert atmosphere

8.1: potassium carbonate; methanol / 1 h / 20 °C / Inert atmosphere

With methanol; dmap; lithium aluminium tetrahydride; trimethylsilyl acetate; di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; trifluoroacetic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene; 4.1: |Keck Asymmetric Allylation / 4.2: |Keck Asymmetric Allylation / 4.3: |Keck Asymmetric Allylation / 7.1: |Mitsunobu Displacement;

DOI:10.1016/j.tetlet.2016.06.102

Reference yield:

4-(3-hydroxypropyl)phenyl acetate (107866-55-7) → (1S,3S,5S)-1,7-bis(4-hydroxyphenyl)-1,5-epoxy-3-hydroxyheptane (1415609-84-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 20 °C / Inert atmosphere

2.1: trifluoroacetic acid / dichloromethane / 4 h / Inert atmosphere; Reflux; Molecular sieve

2.2: 0.5 h / 20 °C / Inert atmosphere; Molecular sieve

2.3: 72 h / -78 - -20 °C / Inert atmosphere; Molecular sieve

3.1: trimethylsilyl acetate; acetic acid; boron trifluoride diethyl etherate / dichloromethane / 0 - 20 °C / Inert atmosphere

4.1: potassium carbonate; methanol / 1 h / 20 °C / Inert atmosphere

5.1: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 20 °C / Inert atmosphere

6.1: potassium carbonate; methanol / 1 h / 20 °C / Inert atmosphere

With methanol; trimethylsilyl acetate; di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; potassium carbonate; acetic acid; triphenylphosphine; trifluoroacetic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dichloromethane; dimethyl sulfoxide; toluene; 2.1: |Keck Asymmetric Allylation / 2.2: |Keck Asymmetric Allylation / 2.3: |Keck Asymmetric Allylation / 5.1: |Mitsunobu Displacement;

DOI:10.1016/j.tetlet.2016.06.102

upstream raw materials:

ethyl 3-(4-hydroxyphenyl)prop-2-enoate

3-(4-hydroxy-phenyl)-propionic acid ethyl ester

3-(4-hydroxyphenyl)propan-1-ol

4-(3-hydroxypropyl)phenyl acetate

Refernces