4,6-(S)-dimethyl-7-(4'-N,N-dimethylaminophenyl)-7-hydroxy-2,4-heptadienoic acid

Base Information

• Chemical Name: 4,6-(S)-dimethyl-7-(4'-N,N-dimethylaminophenyl)-7-hydroxy-2,4-heptadienoic acid
• CAS No.: 122222-85-9
• Molecular Formula: C₁₇H₂₃NO₃
• Molecular Weight: 289.375
• Mol file: 122222-85-9.mol

Synonyms:

Chemical Property of 4,6-(S)-dimethyl-7-(4'-N,N-dimethylaminophenyl)-7-hydroxy-2,4-heptadienoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,6-(S)-dimethyl-7-(4'-N,N-dimethylaminophenyl)-7-hydroxy-2,4-heptadienoic acid

There total 16 articles about 4,6-(S)-dimethyl-7-(4'-N,N-dimethylaminophenyl)-7-hydroxy-2,4-heptadienoic acid 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: 80.0%

methyl 4,6-(R)-dimethyl-7-(4'-N,N-dimethylaminophenyl)-7-(2-methoxypropyloxy)-2,4-heptadienoate (122222-84-8,122223-00-1,122223-01-2,122292-84-6,125244-90-8) → 4,6-(R)-dimethyl-7-(4'-N,N-dimethylaminophenyl)-7-hydroxy-2,4-heptadienoic acid (122222-85-9,122222-86-0,122223-02-3,122223-03-4,125936-83-6)

Guidance literature:

With lithium hydroxide; In methanol; at 45 ℃; for 12h;

DOI:10.1016/S0040-4020(01)89789-1

Reference yield:

methyl 4,6-(S)-dimethyl-7-(4'-N,N-dimethylaminophenyl)-7-(2-methoxypropyloxy)-2,4-heptadienoate (122222-84-8,122223-00-1,122223-01-2,122292-84-6,125244-90-8) → 4,6-(S)-dimethyl-7-(4'-N,N-dimethylaminophenyl)-7-hydroxy-2,4-heptadienoic acid (122222-85-9,122222-86-0,122223-02-3,122223-03-4,125936-83-6)

Guidance literature:

With lithium hydroxide; In methanol; at 45 ℃; for 12h; Yield given;

DOI:10.1016/S0040-4020(01)89789-1

Reference yield:

(R)-3-(4-Dimethylamino-phenyl)-3-(1-methoxy-1-methyl-ethoxy)-2-methyl-propionaldehyde (122222-78-0,122222-94-0,125244-86-2) → 4,6-(R)-dimethyl-7-(4'-N,N-dimethylaminophenyl)-7-hydroxy-2,4-heptadienoic acid (122222-85-9,122222-86-0,122223-02-3,122223-03-4,125936-83-6)

Guidance literature:

Multi-step reaction with 5 steps

1: CH₂Cl₂ / 6 h / Heating

2: 89 percent / DIBAL-H / toluene; hexane / 0.5 h / -78 °C

3: Et₃N, SO₃-C₅H₅N, DMSO / Ambient temperature

4: CH₂Cl₂ / 24 h / Heating

5: 80 percent / aq. LiOH / methanol / 12 h / 45 °C

With lithium hydroxide; pyridine-SO₃ complex; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In methanol; hexane; dichloromethane; toluene;

DOI:10.1016/S0040-4020(01)89789-1

upstream raw materials:

methyl 4,6-(R)-dimethyl-7-(4'-N,N-dimethylaminophenyl)-7-(2-methoxypropyloxy)-2,4-heptadienoate

(R)-3-(4-Dimethylamino-phenyl)-3-(1-methoxy-1-methyl-ethoxy)-2-methyl-propionaldehyde

3-t-butyldimethylsilyloxy-1-(4'-N,N-dimethylaminophenyl)-2-(R)-methyl-1-propanol

3-(4'-N,N-dimethylaminophenyl)-3-(2-methoxypropyloxy)-2-(R)-methyl-1-propanol

Downstream raw materials:

(+)-(R)-trichostatin acid

trichostatin A

(S)-(-)-trichostatin A

O-(2-methoxypropyl)-(R)-trichostatin A