<1R,4S,5R-(E)>-4-(5-Acetoxy-3-methylpent-3-en-1-ynyl)-4-hydroxy-3,3,5-trimethylcyclohexyl acetate

Base Information

• Chemical Name: <1R,4S,5R-(E)>-4-(5-Acetoxy-3-methylpent-3-en-1-ynyl)-4-hydroxy-3,3,5-trimethylcyclohexyl acetate
• CAS No.: 70905-70-3
• Molecular Formula: C₁₉H₂₈O₅
• Molecular Weight: 336.428
• Mol file: 70905-70-3.mol

Synonyms:<1R,4S,5R-(E)>-4-(5-Acetoxy-3-methylpent-3-en-1-ynyl)-4-hydroxy-3,3,5-trimethylcyclohexyl acetate

Chemical Property of <1R,4S,5R-(E)>-4-(5-Acetoxy-3-methylpent-3-en-1-ynyl)-4-hydroxy-3,3,5-trimethylcyclohexyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <1R,4S,5R-(E)>-4-(5-Acetoxy-3-methylpent-3-en-1-ynyl)-4-hydroxy-3,3,5-trimethylcyclohexyl acetate

There total 20 articles about <1R,4S,5R-(E)>-4-(5-Acetoxy-3-methylpent-3-en-1-ynyl)-4-hydroxy-3,3,5-trimethylcyclohexyl acetate 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: 98.0%

acetic anhydride (108-24-7) + (1S,4R,6R)-1-<(E)-5-hydroxy-3-methylpent-3-en-1-ynyl>-2,2,6-trimethylcyclohexane-1,4-diol (70905-68-9) → <1R,4S,5R-(E)>-4-(5-Acetoxy-3-methylpent-3-en-1-ynyl)-4-hydroxy-3,3,5-trimethylcyclohexyl acetate (70905-70-3)

Guidance literature:

With pyridine; at 20 ℃; for 24h;

DOI:10.1016/0957-4166(94)80179-7

Reference yield: 60.0%

acetic anhydride (108-24-7) + 2-trans-5-(1',4'-dihydroxy-2',2',6'-trimethylcyclohexyl)-3-methylpent-2-en-4-yn-1-ol (26533-75-5,70905-68-9,81844-60-2,91796-24-6,95343-63-8,130696-71-8,130696-72-9) → Acetic acid (1R,4S,5R)-4-((Z)-5-acetoxy-3-methyl-pent-3-en-1-ynyl)-4-hydroxy-3,3,5-trimethyl-cyclohexyl ester (70905-70-3,95403-81-9,95403-82-0)

Guidance literature:

In pyridine;

Reference yield:

(4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexan-1-one (20548-02-1,55058-51-0,60686-81-9,60686-82-0,82977-53-5,90082-06-7,90129-05-8,99881-84-2,60046-50-6) → <1R,4S,5R-(E)>-4-(5-Acetoxy-3-methylpent-3-en-1-ynyl)-4-hydroxy-3,3,5-trimethylcyclohexyl acetate (70905-70-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / triethylamine / diethyl ether / 15 h / 0 - 20 °C

2: 1.) EtMgBr / 1.) diethyl ether, THF, reflux, 30 min, 2.) diethyl ether, THF, reflux, 20 h

3: 5percent potassium hydroxide / methanol / 2 h / 20 °C

4: 98 percent / pyridine / 24 h / 20 °C

With pyridine; potassium hydroxide; ethylmagnesium bromide; triethylamine; In methanol; diethyl ether;

DOI:10.1016/0957-4166(94)80179-7

upstream raw materials:

acetic anhydride

2-cis-5-(1',4'-dihydroxy-2',2',6'-trimethylcyclohexyl)-3-methylpent-2-en-4-yn-1-ol

2-trans-5-(1',4'-dihydroxy-2',2',6'-trimethylcyclohexyl)-3-methylpent-2-en-4-yn-1-ol

2,2,6-trimethyl-1,4-cyclohexanedione 4-ethylene acetal

Downstream raw materials:

2-trans-1-acetoxy-5-(4'-acetoxy-2',2',6'-trimethylcyclohex-1'-enyl)-3-methylpent-2-en-4-yne

2-trans-5-<(4'R)-4'-acetoxy-2',6',6'-trimethylcyclohex-1'-enyl>-3-methyl-2-penten-4-yn-1-yl acetate

Acetic acid (1R,5R)-4-[(E)-5-acetoxy-3-methyl-2-oxo-pent-3-en-(Z)-ylidene]-3,3,5-trimethyl-cyclohexyl ester

Acetic acid (1R,5R)-4-[(E)-5-acetoxy-3-methyl-2-oxo-pent-3-en-(E)-ylidene]-3,3,5-trimethyl-cyclohexyl ester