(5R,8S)-1-Benzyloxy-5-((E)-(S)-1,5-dimethyl-hexa-2,4-dienyl)-8a-hydroxy-3,8-dimethyl-octahydro-naphthalen-2-one

Base Information

• Chemical Name: (5R,8S)-1-Benzyloxy-5-((E)-(S)-1,5-dimethyl-hexa-2,4-dienyl)-8a-hydroxy-3,8-dimethyl-octahydro-naphthalen-2-one
• CAS No.: 219566-61-7
• Molecular Formula: C₂₇H₃₈O₃
• Molecular Weight: 410.597
• Mol file: 219566-61-7.mol

Synonyms:(5R,8S)-1-Benzyloxy-5-((E)-(S)-1,5-dimethyl-hexa-2,4-dienyl)-8a-hydroxy-3,8-dimethyl-octahydro-naphthalen-2-one

Chemical Property of (5R,8S)-1-Benzyloxy-5-((E)-(S)-1,5-dimethyl-hexa-2,4-dienyl)-8a-hydroxy-3,8-dimethyl-octahydro-naphthalen-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,8S)-1-Benzyloxy-5-((E)-(S)-1,5-dimethyl-hexa-2,4-dienyl)-8a-hydroxy-3,8-dimethyl-octahydro-naphthalen-2-one

There total 9 articles about (5R,8S)-1-Benzyloxy-5-((E)-(S)-1,5-dimethyl-hexa-2,4-dienyl)-8a-hydroxy-3,8-dimethyl-octahydro-naphthalen-2-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: 70.0%

(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) → (5R,8S)-1-Benzyloxy-5-((E)-(S)-1,5-dimethyl-hexa-2,4-dienyl)-8a-hydroxy-3,8-dimethyl-octahydro-naphthalen-2-one (219566-61-7)

Guidance literature:

With potassium hydroxide; In ethanol; at 0 ℃; for 1h;

DOI:10.1021/ja983041s

Reference yield:

(+/-)-1-benzyloxy-3-methyl-but-3-en-2-ol (71312-19-1) → (5R,8S)-1-Benzyloxy-5-((E)-(S)-1,5-dimethyl-hexa-2,4-dienyl)-8a-hydroxy-3,8-dimethyl-octahydro-naphthalen-2-one (219566-61-7)

Guidance literature:

Multi-step reaction with 3 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

3: 70 percent / KOH / ethanol / 1 h / 0 °C

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

DOI:10.1021/ja983041s

Reference yield:

Benzyloxymethyl isopropenyl ketone (103791-04-4) → (5R,8S)-1-Benzyloxy-5-((E)-(S)-1,5-dimethyl-hexa-2,4-dienyl)-8a-hydroxy-3,8-dimethyl-octahydro-naphthalen-2-one (219566-61-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / SnCl₄ / CH₂Cl₂ / 0.67 h / -78 °C

2: 70 percent / KOH / ethanol / 1 h / 0 °C

With potassium hydroxide; tin(IV) chloride; In ethanol; dichloromethane;

DOI:10.1021/ja983041s

upstream raw materials:

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

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

Benzyloxymethyl isopropenyl ketone

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-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one

(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

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-yloxy]-tert-butyl-dimethyl-silane