(3R,6S)-2-(4-Benzyloxy-2-methyl-3-oxo-butyl)-3-((E)-(S)-1,5-dimethyl-hexa-2,4-dienyl)-6-methyl-cyclohexanone

Base Information

• Chemical Name: (3R,6S)-2-(4-Benzyloxy-2-methyl-3-oxo-butyl)-3-((E)-(S)-1,5-dimethyl-hexa-2,4-dienyl)-6-methyl-cyclohexanone
• CAS No.: 219498-10-9
• Molecular Formula: C₂₇H₃₈O₃
• Molecular Weight: 410.597
• Mol file: 219498-10-9.mol

Synonyms:(3R,6S)-2-(4-Benzyloxy-2-methyl-3-oxo-butyl)-3-((E)-(S)-1,5-dimethyl-hexa-2,4-dienyl)-6-methyl-cyclohexanone

Chemical Property of (3R,6S)-2-(4-Benzyloxy-2-methyl-3-oxo-butyl)-3-((E)-(S)-1,5-dimethyl-hexa-2,4-dienyl)-6-methyl-cyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,6S)-2-(4-Benzyloxy-2-methyl-3-oxo-butyl)-3-((E)-(S)-1,5-dimethyl-hexa-2,4-dienyl)-6-methyl-cyclohexanone

There total 7 articles about (3R,6S)-2-(4-Benzyloxy-2-methyl-3-oxo-butyl)-3-((E)-(S)-1,5-dimethyl-hexa-2,4-dienyl)-6-methyl-cyclohexanone 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: 58.0%

Benzyloxymethyl isopropenyl ketone (103791-04-4) + [(3R,6S)-3-((E)-(S)-1,5-Dimethyl-hexa-2,4-dienyl)-6-methyl-cyclohex-1-enyloxy]-trimethyl-silane (219498-08-5) → (3R,6S)-2-(4-Benzyloxy-2-methyl-3-oxo-butyl)-3-((E)-(S)-1,5-dimethyl-hexa-2,4-dienyl)-6-methyl-cyclohexanone (219498-10-9)

Guidance literature:

With tin(IV) chloride; In dichloromethane; at -78 ℃; for 0.666667h;

DOI:10.1021/ja983041s

Reference yield:

(+/-)-1-benzyloxy-3-methyl-but-3-en-2-ol (71312-19-1) → (3R,6S)-2-(4-Benzyloxy-2-methyl-3-oxo-butyl)-3-((E)-(S)-1,5-dimethyl-hexa-2,4-dienyl)-6-methyl-cyclohexanone (219498-10-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) oxalyl chloride, DMSO, 2.) iPr₂NH / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, -78 deg C, 15 min

2: 58 percent / SnCl₄ / CH₂Cl₂ / 0.67 h / -78 °C

With oxalyl dichloride; tin(IV) chloride; dimethyl sulfoxide; diisopropylamine; In dichloromethane;

DOI:10.1021/ja983041s

Reference yield:

bis(3-methyl-2-butenyl)diphenylphosphonium bromide (27387-41-3) → (3R,6S)-2-(4-Benzyloxy-2-methyl-3-oxo-butyl)-3-((E)-(S)-1,5-dimethyl-hexa-2,4-dienyl)-6-methyl-cyclohexanone (219498-10-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) t-BuOK / 1.) DME, 0 deg C, 2.) DME, -60 deg C, 10 min

2: 100 percent / LDA / 1,2-dimethoxy-ethane; hexane / 0.08 h / -78 °C

3: 58 percent / SnCl₄ / CH₂Cl₂ / 0.67 h / -78 °C

With potassium tert-butylate; tin(IV) chloride; lithium diisopropyl amide; In 1,2-dimethoxyethane; hexane; dichloromethane;

DOI:10.1021/ja983041s

upstream raw materials:

Benzyloxymethyl isopropenyl ketone

[(3R,6S)-3-((E)-(S)-1,5-Dimethyl-hexa-2,4-dienyl)-6-methyl-cyclohex-1-enyloxy]-trimethyl-silane

(+/-)-1-benzyloxy-3-methyl-but-3-en-2-ol

bis(3-methyl-2-butenyl)diphenylphosphonium bromide

Downstream raw materials:

[(5R,8S)-1-Benzyloxy-5-((E)-(S)-1,5-dimethyl-hexa-2,4-dienyl)-3,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yloxy]-tert-butyl-dimethyl-silane

Methanesulfonic acid (5R,8S)-1-benzyloxy-5-((E)-(S)-1,5-dimethyl-hexa-2,4-dienyl)-3,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl ester

(5R,8S)-1-Benzyloxy-5-((E)-(S)-1,5-dimethyl-hexa-2,4-dienyl)-3,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ol

(5R,8S)-1-Benzyloxy-5-((E)-(S)-1,5-dimethyl-hexa-2,4-dienyl)-3,8-dimethyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one