(2E,4E,10E)-(6S,7S,8R,9S)-7,9-Dimethoxy-3,6,8-trimethyl-11-phenyl-undeca-2,4,10-trienoic acid (2,6-dihydroxy-1-trimethylsilanyl-hexyl)-amide

Base Information

• Chemical Name: (2E,4E,10E)-(6S,7S,8R,9S)-7,9-Dimethoxy-3,6,8-trimethyl-11-phenyl-undeca-2,4,10-trienoic acid (2,6-dihydroxy-1-trimethylsilanyl-hexyl)-amide
• CAS No.: 443123-82-8
• Molecular Formula: C₃₁H₅₁NO₅Si
• Molecular Weight: 545.835
• Mol file: 443123-82-8.mol

Synonyms:(2E,4E,10E)-(6S,7S,8R,9S)-7,9-Dimethoxy-3,6,8-trimethyl-11-phenyl-undeca-2,4,10-trienoic acid (2,6-dihydroxy-1-trimethylsilanyl-hexyl)-amide

Chemical Property of (2E,4E,10E)-(6S,7S,8R,9S)-7,9-Dimethoxy-3,6,8-trimethyl-11-phenyl-undeca-2,4,10-trienoic acid (2,6-dihydroxy-1-trimethylsilanyl-hexyl)-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,4E,10E)-(6S,7S,8R,9S)-7,9-Dimethoxy-3,6,8-trimethyl-11-phenyl-undeca-2,4,10-trienoic acid (2,6-dihydroxy-1-trimethylsilanyl-hexyl)-amide

There total 9 articles about (2E,4E,10E)-(6S,7S,8R,9S)-7,9-Dimethoxy-3,6,8-trimethyl-11-phenyl-undeca-2,4,10-trienoic acid (2,6-dihydroxy-1-trimethylsilanyl-hexyl)-amide 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:

5-(tert-butyldimethyl-silyloxy)pentan-1-ol (83067-20-3) → (2E,4E,10E)-(6S,7S,8R,9S)-7,9-Dimethoxy-3,6,8-trimethyl-11-phenyl-undeca-2,4,10-trienoic acid (2,6-dihydroxy-1-trimethylsilanyl-hexyl)-amide (443123-82-8)

Guidance literature:

Multi-step reaction with 9 steps

1: (COCl)2; Et₃N; DMSO / CH₂Cl₂ / -78 °C

2: PPh₃; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

3: nBuLi / tetrahydrofuran / 0.5 h / -78 °C

4: camphorsulfonic acid / methanol; CH₂Cl₂ / 0.5 h / 0 °C

5: H₂ / Lindlar's catalyst / hexane

6: 79 percent / mCPBA / CH₂Cl₂ / 0.75 h / 0 - 20 °C

7: 88 percent / NaN₃; NH₄Cl / methanol; H₂O / 15 h / 0 - 20 °C

8: LiAlH₄ / diethyl ether / 2 h / 0 - 20 °C

9: EDCI; HOBt / CH₂Cl₂ / 5.25 h / 0 - 20 °C

With lithium aluminium tetrahydride; n-butyllithium; sodium azide; oxalyl dichloride; camphor-10-sulfonic acid; hydrogen; ammonium chloride; benzotriazol-1-ol; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; 1: Swern oxidation;

DOI:10.1016/S0040-4039(02)00289-7

Reference yield:

5-tert-butyldimethylsilyloxypentanal (87184-80-3) → (2E,4E,10E)-(6S,7S,8R,9S)-7,9-Dimethoxy-3,6,8-trimethyl-11-phenyl-undeca-2,4,10-trienoic acid (2,6-dihydroxy-1-trimethylsilanyl-hexyl)-amide (443123-82-8)

Guidance literature:

Multi-step reaction with 8 steps

1: PPh₃; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2: nBuLi / tetrahydrofuran / 0.5 h / -78 °C

3: camphorsulfonic acid / methanol; CH₂Cl₂ / 0.5 h / 0 °C

4: H₂ / Lindlar's catalyst / hexane

5: 79 percent / mCPBA / CH₂Cl₂ / 0.75 h / 0 - 20 °C

6: 88 percent / NaN₃; NH₄Cl / methanol; H₂O / 15 h / 0 - 20 °C

7: LiAlH₄ / diethyl ether / 2 h / 0 - 20 °C

8: EDCI; HOBt / CH₂Cl₂ / 5.25 h / 0 - 20 °C

With lithium aluminium tetrahydride; n-butyllithium; sodium azide; camphor-10-sulfonic acid; hydrogen; ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water;

DOI:10.1016/S0040-4039(02)00289-7

Reference yield:

6-trimethylsilanyl-hex-5-yn-1-ol (103437-52-1) → (2E,4E,10E)-(6S,7S,8R,9S)-7,9-Dimethoxy-3,6,8-trimethyl-11-phenyl-undeca-2,4,10-trienoic acid (2,6-dihydroxy-1-trimethylsilanyl-hexyl)-amide (443123-82-8)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / Lindlar's catalyst / hexane

2: 79 percent / mCPBA / CH₂Cl₂ / 0.75 h / 0 - 20 °C

3: 88 percent / NaN₃; NH₄Cl / methanol; H₂O / 15 h / 0 - 20 °C

4: LiAlH₄ / diethyl ether / 2 h / 0 - 20 °C

5: EDCI; HOBt / CH₂Cl₂ / 5.25 h / 0 - 20 °C

With lithium aluminium tetrahydride; sodium azide; hydrogen; ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-chloro-benzenecarboperoxoic acid; Lindlar's catalyst; In methanol; diethyl ether; hexane; dichloromethane; water;

DOI:10.1016/S0040-4039(02)00289-7

upstream raw materials:

(2E,4E,6S,7S,8R,9S,10E)-7,9-dimethoxy-3,6,8-trimethyl-11-phenylundeca-2,4,10-trienoic acid

6-amino-6-trimethylsilanyl-hexane-1,5-diol

5-(tert-butyldimethyl-silyloxy)pentan-1-ol

5-tert-butyldimethylsilyloxypentanal

Downstream raw materials:

(2E,4E,10E)-(6S,7S,8R,9S)-7,9-Dimethoxy-3,6,8-trimethyl-11-phenyl-undeca-2,4,10-trienoic acid ((Z)-6-hydroxy-hex-1-enyl)-amide

(2E,4E,10E)-(6S,7S,8R,9S)-7,9-Dimethoxy-3,6,8-trimethyl-11-phenyl-undeca-2,4,10-trienoic acid [2-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-1-trimethylsilanyl-hexyl]-amide

5-(tert-Butyl-dimethyl-silanyloxy)-6-((2E,4E,10E)-(6S,7S,8R,9S)-7,9-dimethoxy-3,6,8-trimethyl-11-phenyl-undeca-2,4,10-trienoylamino)-6-trimethylsilanyl-hexanoic acid

[5-(tert-Butyl-dimethyl-silanyloxy)-6-((2E,4E,10E)-(6S,7S,8R,9S)-7,9-dimethoxy-3,6,8-trimethyl-11-phenyl-undeca-2,4,10-trienoylamino)-6-trimethylsilanyl-hexanoylamino]-acetic acid methyl ester