(3R,5S)-1-(4-(benzyloxy)-3-methoxyphenyl)decane-3,5-diol

Base Information

• Chemical Name: (3R,5S)-1-(4-(benzyloxy)-3-methoxyphenyl)decane-3,5-diol
• CAS No.: 1360109-92-7
• Molecular Formula: C₂₄H₃₄O₄
• Molecular Weight: 386.532
• Mol file: 1360109-92-7.mol

Synonyms:(3R,5S)-1-(4-(benzyloxy)-3-methoxyphenyl)decane-3,5-diol

Chemical Property of (3R,5S)-1-(4-(benzyloxy)-3-methoxyphenyl)decane-3,5-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5S)-1-(4-(benzyloxy)-3-methoxyphenyl)decane-3,5-diol

There total 13 articles about (3R,5S)-1-(4-(benzyloxy)-3-methoxyphenyl)decane-3,5-diol 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: 90.0%

(4R,6S)-4-(4-(benzyloxy)-3-methoxyphenethyl)-2,2-dimethyl-6-pentyl-1,3-dioxane (1360109-90-5) → (3R,5S)-1-(4-(benzyloxy)-3-methoxyphenyl)decane-3,5-diol (1360109-92-7)

Guidance literature:

With methanol; toluene-4-sulfonic acid; at 0 - 20 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tetasy.2011.11.010

Reference yield:

(S)-1-(4-(benzyloxy)-3-methoxyphenyl)-5-(tert-butyldimethylsilyloxy)dec-1-yn-3-one (1360109-86-9) → (3R,5S)-1-(4-(benzyloxy)-3-methoxyphenyl)decane-3,5-diol (1360109-92-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: hydrogen; palladium(II) hydroxide / benzene / 5 h / 20 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 0 °C / Inert atmosphere

3.1: diethyl methoxy borane / tetrahydrofuran; methanol / 0.5 h / -78 °C / Inert atmosphere

3.2: 6 h / -78 °C / Inert atmosphere

4.1: toluene-4-sulfonic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere

5.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

5.2: Inert atmosphere

6.1: methanol; toluene-4-sulfonic acid / 1 h / 0 - 20 °C / Inert atmosphere

With methanol; diethyl methoxy borane; tetrabutyl ammonium fluoride; hydrogen; palladium(II) hydroxide; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1016/j.tetasy.2011.11.010

Reference yield:

C15H34O3Si → (3R,5S)-1-(4-(benzyloxy)-3-methoxyphenyl)decane-3,5-diol (1360109-92-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: sodium periodate / tetrahydrofuran; water / 1 h

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

2.2: 4 h / -78 - 20 °C

3.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

4.1: hydrogen; palladium(II) hydroxide / benzene / 5 h / 20 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 0 °C / Inert atmosphere

6.1: diethyl methoxy borane / tetrahydrofuran; methanol / 0.5 h / -78 °C / Inert atmosphere

6.2: 6 h / -78 °C / Inert atmosphere

7.1: toluene-4-sulfonic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere

8.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

8.2: Inert atmosphere

9.1: methanol; toluene-4-sulfonic acid / 1 h / 0 - 20 °C / Inert atmosphere

With methanol; sodium periodate; n-butyllithium; diethyl methoxy borane; tetrabutyl ammonium fluoride; hydrogen; palladium(II) hydroxide; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; hexane; dichloromethane; water; benzene;

DOI:10.1016/j.tetasy.2011.11.010

upstream raw materials:

(S)-1-(4-(benzyloxy)-3-methoxyphenyl)-5-(tert-butyldimethylsilyloxy)dec-1-yn-3-one

C₃₀H₄₄O₄Si

(5S)-5-{[tert-butyl(dimethyl)silyl]oxy}-1-(4-hydroxy-3-methoxyphenyl)decan-3-one

(4R,6S)-4-(4-(benzyloxy)-3-methoxyphenethyl)-2,2-dimethyl-6-pentyl-1,3-dioxane

Downstream raw materials:

(3R,5S)-1-(4-hydroxy-3-methoxyphenyl)decane-3,5-diyl diacetate

(3R,5S)-1-(4-(benzyloxy)-3-methoxyphenyl)decane-3,5-diyl diacetate

Refernces