(1S,4aR,5R,6S,8aR)-5-((4-methoxybenzyl)oxy)-6-(methoxymethyl)-1,2,4a,5,6,8a-hexahydronaphthalen-1-ol

Base Information

• Chemical Name: (1S,4aR,5R,6S,8aR)-5-((4-methoxybenzyl)oxy)-6-(methoxymethyl)-1,2,4a,5,6,8a-hexahydronaphthalen-1-ol
• CAS No.: 1167993-24-9
• Molecular Formula: C₂₀H₂₆O₄
• Molecular Weight: 330.424
• Mol file: 1167993-24-9.mol

Synonyms:(1S,4aR,5R,6S,8aR)-5-((4-methoxybenzyl)oxy)-6-(methoxymethyl)-1,2,4a,5,6,8a-hexahydronaphthalen-1-ol

Chemical Property of (1S,4aR,5R,6S,8aR)-5-((4-methoxybenzyl)oxy)-6-(methoxymethyl)-1,2,4a,5,6,8a-hexahydronaphthalen-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4aR,5R,6S,8aR)-5-((4-methoxybenzyl)oxy)-6-(methoxymethyl)-1,2,4a,5,6,8a-hexahydronaphthalen-1-ol

There total 11 articles about (1S,4aR,5R,6S,8aR)-5-((4-methoxybenzyl)oxy)-6-(methoxymethyl)-1,2,4a,5,6,8a-hexahydronaphthalen-1-ol 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: 85.0%

(1R,4S,4aS,5R,6R,8aS)-5-((4-methoxybenzyl)oxy)-6-(methoxymethyl)-1,4,4a,5,6,8a-hexahydro-1,4-epoxynaphthalene (1167993-21-6) → (1S,4aR,5R,6S,8aR)-5-((4-methoxybenzyl)oxy)-6-(methoxymethyl)-1,2,4a,5,6,8a-hexahydronaphthalen-1-ol (1167993-24-9) + (1S,4aS,7R,8R,8aR)-8-((4-methoxybenzyl)oxy)-7-(methoxymethyl)-1,2,4a,7,8,8a-hexahydronaphthalen-1-ol (1167993-12-5)

Guidance literature:

(1R,4S,4aS,5R,6R,8aS)-5-((4-methoxybenzyl)oxy)-6-(methoxymethyl)-1,4,4a,5,6,8a-hexahydro-1,4-epoxynaphthalene; With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; In toluene; for 0.5h; Inert atmosphere;

With diisobutylaluminium hydride; In hexane; toluene; at 22 ℃; for 6h; Inert atmosphere;

With Rochelle's salt; In hexane; toluene; for 0.5h; Inert atmosphere;

DOI:10.1021/ol900834c

Reference yield:

(1R*,4S*,4aS*,5R*,6R*,8aS*)-5-((4-methoxybenzyl)oxy)-6-(methoxymethyl)-1,4,4a,5,6,8a-hexahydro-1,4-epoxynaphthalene → (1S,4aR,5R,6S,8aR)-5-((4-methoxybenzyl)oxy)-6-(methoxymethyl)-1,2,4a,5,6,8a-hexahydronaphthalen-1-ol (1167993-24-9) + (1R,4aS,5S,6R,8aS)-5-((4-methoxybenzyl)oxy)-6-(methoxymethyl)-1,2,4a,5,6,8a-hexahydronaphthalen-1-ol (1167993-13-6) + (1R,4aR,7S,8S,8aS)-8-((4-methoxybenzyl)oxy)-7-(methoxymethyl)-1,2,4a,7,8,8a-hexahydronaphthalen-1-ol (1167993-23-8) + (1S,4aS,7R,8R,8aR)-8-((4-methoxybenzyl)oxy)-7-(methoxymethyl)-1,2,4a,7,8,8a-hexahydronaphthalen-1-ol (1167993-12-5)

Guidance literature:

(1R*,4S*,4aS*,5R*,6R*,8aS*)-5-((4-methoxybenzyl)oxy)-6-(methoxymethyl)-1,4,4a,5,6,8a-hexahydro-1,4-epoxynaphthalene; With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; In toluene; for 0.5h; Inert atmosphere;

With diisobutylaluminium hydride; In hexane; toluene; at 22 ℃; for 6h; Inert atmosphere;

With Rochelle's salt; In hexane; toluene; for 0.5h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ol900834c

Reference yield:

(1R*,4S*,4aS*,5S*,6S*,8aS*)-6-((dimethyl(phenyl)silyl)methyl)-1,4,4a,5,6,8a-hexahydro-1,4-epoxynaphthalen-5-ol → (1S,4aR,5R,6S,8aR)-5-((4-methoxybenzyl)oxy)-6-(methoxymethyl)-1,2,4a,5,6,8a-hexahydronaphthalen-1-ol (1167993-24-9) + (1R,4aS,5S,6R,8aS)-5-((4-methoxybenzyl)oxy)-6-(methoxymethyl)-1,2,4a,5,6,8a-hexahydronaphthalen-1-ol (1167993-13-6) + (1R,4aR,7S,8S,8aS)-8-((4-methoxybenzyl)oxy)-7-(methoxymethyl)-1,2,4a,7,8,8a-hexahydronaphthalen-1-ol (1167993-23-8) + (1S,4aS,7R,8R,8aR)-8-((4-methoxybenzyl)oxy)-7-(methoxymethyl)-1,2,4a,7,8,8a-hexahydronaphthalen-1-ol (1167993-12-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 8 h / 0 - 20 °C / Inert atmosphere

2.1: tert.-butylhydroperoxide; tetrabutyl ammonium fluoride; potassium hydride / tetrahydrofuran; 1-methyl-pyrrolidin-2-one; decane; hexane; mineral oil / 3 h / 0 - 20 °C / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 12 h / 0 °C / Inert atmosphere

4.1: bis(1,5-cyclooctadiene)nickel⁽⁰⁾; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / toluene / 0.5 h / Inert atmosphere

4.2: 7 h / 22 °C / Inert atmosphere

With tert.-butylhydroperoxide; bis(1,5-cyclooctadiene)nickel⁽⁰⁾; tetrabutyl ammonium fluoride; potassium hydride; sodium hydride; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; decane; hexane; N,N-dimethyl-formamide; toluene; mineral oil;

DOI:10.1002/chem.201200257

upstream raw materials:

(1R,4S,4aS,5R,6R,8aS)-5-((4-methoxybenzyl)oxy)-6-(methoxymethyl)-1,4,4a,5,6,8a-hexahydro-1,4-epoxynaphthalene

C₁₆H₁₃NO₄S

C₁₁H₁₀O₄

p-Methoxybenzyl bromide