(+)-1(Z)-(1R,4R,6S)-1-(5-acetoxy-3-methylpent-3-en-1-ynyl)-2,2,6-trimethylcyclohexan-1,4-diol

Base Information

• Chemical Name: (+)-1(Z)-(1R,4R,6S)-1-(5-acetoxy-3-methylpent-3-en-1-ynyl)-2,2,6-trimethylcyclohexan-1,4-diol
• CAS No.: 130583-99-2
• Molecular Formula: C₁₇H₂₆O₄
• Molecular Weight: 294.391
• Mol file: 130583-99-2.mol

Synonyms:(+)-1(Z)-(1R,4R,6S)-1-(5-acetoxy-3-methylpent-3-en-1-ynyl)-2,2,6-trimethylcyclohexan-1,4-diol

Chemical Property of (+)-1(Z)-(1R,4R,6S)-1-(5-acetoxy-3-methylpent-3-en-1-ynyl)-2,2,6-trimethylcyclohexan-1,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-1(Z)-(1R,4R,6S)-1-(5-acetoxy-3-methylpent-3-en-1-ynyl)-2,2,6-trimethylcyclohexan-1,4-diol

There total 7 articles about (+)-1(Z)-(1R,4R,6S)-1-(5-acetoxy-3-methylpent-3-en-1-ynyl)-2,2,6-trimethylcyclohexan-1,4-diol 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:

Acetic acid (Z)-5-[(1R,4R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-2,2,6-trimethyl-cyclohexyl]-3-methyl-pent-2-en-4-ynyl ester (130584-00-8) → (+)-1(Z)-(1R,4R,6S)-1-(5-acetoxy-3-methylpent-3-en-1-ynyl)-2,2,6-trimethylcyclohexan-1,4-diol (130583-99-2)

Guidance literature:

With water; acetic acid; at 80 ℃; Yield given;

Reference yield:

(Z)-3-methylpent-2-en-4-ynol (6153-05-5,105-29-3) → (+)-1(Z)-(1R,4R,6S)-1-(5-acetoxy-3-methylpent-3-en-1-ynyl)-2,2,6-trimethylcyclohexan-1,4-diol (130583-99-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 64 percent / n-butyl-Li / hexane; tetrahydrofuran / 1) -5 deg C 2) -60 deg C to r.t.

2: pyridine, 4-dimethylaminopyridine / 1 h / Ambient temperature

3: glacical acetic acid, H₂O / 80 °C

With pyridine; dmap; n-butyllithium; water; acetic acid; In tetrahydrofuran; hexane;

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) → (+)-1(Z)-(1R,4R,6S)-1-(5-acetoxy-3-methylpent-3-en-1-ynyl)-2,2,6-trimethylcyclohexan-1,4-diol (130583-99-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 73 percent Turnov_. / 5M NaOH / ethanol / 24 h / 85 °C

2: 99 percent / imidazole / dimethylformamide / Ambient temperature

3: 64 percent / n-butyl-Li / hexane; tetrahydrofuran / 1) -5 deg C 2) -60 deg C to r.t.

4: pyridine, 4-dimethylaminopyridine / 1 h / Ambient temperature

5: glacical acetic acid, H₂O / 80 °C

With pyridine; 1H-imidazole; dmap; sodium hydroxide; n-butyllithium; water; acetic acid; In tetrahydrofuran; ethanol; hexane; N,N-dimethyl-formamide;

upstream raw materials:

Acetic acid (Z)-5-[(1R,4R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-2,2,6-trimethyl-cyclohexyl]-3-methyl-pent-2-en-4-ynyl ester

(Z)-3-methylpent-2-en-4-ynol

(4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexan-1-one

(+)-(4R,6S)-4-hydroxy-2,2,6-trimethylcyclohexanone

Downstream raw materials:

(+)-(4S,5S)-methyl dihydroabscisate

(+)-(4S,5S)-dihydroabscisic acid

(+)-4(Z)-(4R,5S)-4-hydroxy-4-(5-hydroxy-3-methylpent-3-en-1-ynyl)-3,3,5-trimethylcyclohexanone

(+)-4(1E,3Z)-(4S,5S)-4-hydroxy-4-(3-methyl-5-oxo-1,3-pentadienyl)-3,3,5-trimethylcyclohexanone