(1aR,2R,3R,3aS,7aR,7bS)-3-((4-methoxybenzyl)oxy)-2-(methoxymethyl)-1a,2,3,3a,7,7a-hexahydronaphtho[1,2-b]oxiren-4(7bH)-one

Base Information

• Chemical Name: (1aR,2R,3R,3aS,7aR,7bS)-3-((4-methoxybenzyl)oxy)-2-(methoxymethyl)-1a,2,3,3a,7,7a-hexahydronaphtho[1,2-b]oxiren-4(7bH)-one
• CAS No.: 1167993-02-3
• Molecular Formula: C₂₀H₂₄O₅
• Molecular Weight: 344.408

Synonyms:(1aR,2R,3R,3aS,7aR,7bS)-3-((4-methoxybenzyl)oxy)-2-(methoxymethyl)-1a,2,3,3a,7,7a-hexahydronaphtho[1,2-b]oxiren-4(7bH)-one

Chemical Property of (1aR,2R,3R,3aS,7aR,7bS)-3-((4-methoxybenzyl)oxy)-2-(methoxymethyl)-1a,2,3,3a,7,7a-hexahydronaphtho[1,2-b]oxiren-4(7bH)-one

Chemical Property:

Purity/Quality:

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Technology Process of (1aR,2R,3R,3aS,7aR,7bS)-3-((4-methoxybenzyl)oxy)-2-(methoxymethyl)-1a,2,3,3a,7,7a-hexahydronaphtho[1,2-b]oxiren-4(7bH)-one

There total 13 articles about (1aR,2R,3R,3aS,7aR,7bS)-3-((4-methoxybenzyl)oxy)-2-(methoxymethyl)-1a,2,3,3a,7,7a-hexahydronaphtho[1,2-b]oxiren-4(7bH)-one 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: 64.0%

(4aS,7R,8R,8aS)-8-((4-methoxybenzyl)oxy)-7-(methoxymethyl)-4,4a,8,8a-tetrahydronaphthalen-1(7H)-one (1167993-15-8) → (1aS,2R,3R,3aS,7aR,7bR)-3-((4-methoxybenzyl)oxy)-2-(methoxymethyl)-1a,2,3,3a,7,7a-hexahydronaphtho[1,2-b]oxiren-4(7bH)-one (1167993-25-0) + (1aR,2R,3R,3aS,7aR,7bS)-3-((4-methoxybenzyl)oxy)-2-(methoxymethyl)-1a,2,3,3a,7,7a-hexahydronaphtho[1,2-b]oxiren-4(7bH)-one (1167993-02-3) + (1aR,2R,3R,3aS,7aR,7bS)-3-((4-methoxybenzyl)oxy)-2-(methoxymethyl)-1a,2,3,3a,7,7a-hexahydronaphtho[1,2-b]oxiren-4(7bH)-one (1167993-26-1)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 2h; optical yield given as %de; regioselective reaction; Inert atmosphere;

DOI:10.1021/ol900834c

Reference yield:

C16H13NO4S (1167993-07-8) → (1aS,2R,3R,3aS,7aR,7bR)-3-((4-methoxybenzyl)oxy)-2-(methoxymethyl)-1a,2,3,3a,7,7a-hexahydronaphtho[1,2-b]oxiren-4(7bH)-one (1167993-25-0) + (1aR,2R,3R,3aS,7aR,7bS)-3-((4-methoxybenzyl)oxy)-2-(methoxymethyl)-1a,2,3,3a,7,7a-hexahydronaphtho[1,2-b]oxiren-4(7bH)-one (1167993-02-3) + (1aR,2R,3R,3aS,7aR,7bS)-3-((4-methoxybenzyl)oxy)-2-(methoxymethyl)-1a,2,3,3a,7,7a-hexahydronaphtho[1,2-b]oxiren-4(7bH)-one (1167993-26-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: tri-n-butyl-tin hydride / dichloromethane / 0.33 h / 0 °C / Inert atmosphere; Irradiation

2.1: magnesium / diethyl ether; dichloromethane / 2 h / 32 - 35 °C / Inert atmosphere; Sonication; Reflux

2.2: 0.81 h / 20 °C / Inert atmosphere; Sonication

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

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

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

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

6.2: 7 h / 22 °C / Inert atmosphere

7.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / Inert atmosphere

8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.75 h / 40 °C / Inert atmosphere

9.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C / Inert atmosphere

With tert.-butylhydroperoxide; bis(1,5-cyclooctadiene)nickel⁽⁰⁾; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; potassium hydride; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; magnesium; 1,8-diazabicyclo[5.4.0]undec-7-ene; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diethyl ether; decane; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil;

DOI:10.1002/chem.201200257

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 → (1aS,2R,3R,3aS,7aR,7bR)-3-((4-methoxybenzyl)oxy)-2-(methoxymethyl)-1a,2,3,3a,7,7a-hexahydronaphtho[1,2-b]oxiren-4(7bH)-one (1167993-25-0) + (1aR,2R,3R,3aS,7aR,7bS)-3-((4-methoxybenzyl)oxy)-2-(methoxymethyl)-1a,2,3,3a,7,7a-hexahydronaphtho[1,2-b]oxiren-4(7bH)-one (1167993-02-3) + (1aR,2R,3R,3aS,7aR,7bS)-3-((4-methoxybenzyl)oxy)-2-(methoxymethyl)-1a,2,3,3a,7,7a-hexahydronaphtho[1,2-b]oxiren-4(7bH)-one (1167993-26-1)

Guidance literature:

Multi-step reaction with 7 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

5.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / Inert atmosphere

6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.75 h / 40 °C / Inert atmosphere

7.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C / Inert atmosphere

With tert.-butylhydroperoxide; bis(1,5-cyclooctadiene)nickel⁽⁰⁾; tetrabutyl ammonium fluoride; potassium hydride; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; decane; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil;

DOI:10.1002/chem.201200257

upstream raw materials:

(4aS,7R,8R,8aS)-8-((4-methoxybenzyl)oxy)-7-(methoxymethyl)-4,4a,8,8a-tetrahydronaphthalen-1(7H)-one

C₁₆H₁₃NO₄S

(1S,4aS,7R,8R,8aR)-8-((4-methoxybenzyl)oxy)-7-(methoxymethyl)-1,2,4a,7,8,8a-hexahydronaphthalen-1-ol

(4aS,7R,8R,8aS)-8-((4-methoxybenzyl)oxy)-7-(methoxymethyl)-4a,7,8,8atetrahydronaphthalen-1(2H)-one

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