(2E,8E)-(4S,6S,7S)-2,4,6-trimethyl-7-(benzyloxy)-2,8,10-undecatrienal

Base Information

• Chemical Name: (2E,8E)-(4S,6S,7S)-2,4,6-trimethyl-7-(benzyloxy)-2,8,10-undecatrienal
• CAS No.: 107241-77-0
• Molecular Formula: C₂₁H₂₈O₂
• Molecular Weight: 312.452
• Mol file: 107241-77-0.mol

Synonyms:(2E,8E)-(4S,6S,7S)-2,4,6-trimethyl-7-(benzyloxy)-2,8,10-undecatrienal

Chemical Property of (2E,8E)-(4S,6S,7S)-2,4,6-trimethyl-7-(benzyloxy)-2,8,10-undecatrienal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,8E)-(4S,6S,7S)-2,4,6-trimethyl-7-(benzyloxy)-2,8,10-undecatrienal

There total 11 articles about (2E,8E)-(4S,6S,7S)-2,4,6-trimethyl-7-(benzyloxy)-2,8,10-undecatrienal 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: 89.0%

(2E,8E)-(4S,6S,7S)-2,4,6-trimethyl-7-(benzyloxy)-2,8,10-undecatrien-1-ol (107173-32-0) → (2E,8E)-(4S,6S,7S)-2,4,6-trimethyl-7-(benzyloxy)-2,8,10-undecatrienal (107241-77-0)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 0.5h;

DOI:10.1021/jo00383a012

Reference yield:

(2S,4S)-5-<(tert-butyldimethylsilyl)oxy>-2,4-dimethyl-pentanal (107173-24-0) → (2E,8E)-(4S,6S,7S)-2,4,6-trimethyl-7-(benzyloxy)-2,8,10-undecatrienal (107241-77-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 25 min, 2.) THF, hexane, -78 deg C, 1.5 h

2: 79 percent / Red-Al / diethyl ether / 1 h / Ambient temperature

3: 1.) 1,10-phenanthroline, n-BuLi / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, HMPA, -78 deg C, 5 min

4: 99 percent / tetrabutylammonium fluoride / hexane / 6 h / Ambient temperature

5: 82 percent / oxalyl chloride, Me₂SO, Et₃N / CH₂Cl₂ / 30 h / -78 °C

6: 97 percent / CH₂Cl₂ / 72 h / Ambient temperature

7: 100 percent / DIBAH / diethyl ether; hexane / 0.58 h / -78 °C

8: 89 percent / oxylal chloride, Me₂SO / CH₂Cl₂ / 0.5 h / -78 °C

With n-butyllithium; 1,10-Phenanthroline; oxalyl dichloride; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In diethyl ether; hexane; dichloromethane;

DOI:10.1021/jo00383a012

Reference yield:

(2S,4S)-5-<(tert-butyldimethylsilyl)oxy>-2,4-dimethyl-pentan-1-ol (107173-23-9) → (2E,8E)-(4S,6S,7S)-2,4,6-trimethyl-7-(benzyloxy)-2,8,10-undecatrienal (107241-77-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 91 percent / oxalyl chloride, Me₂SO / CH₂Cl₂ / 0.75 h / -78 °C

2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 25 min, 2.) THF, hexane, -78 deg C, 1.5 h

3: 79 percent / Red-Al / diethyl ether / 1 h / Ambient temperature

4: 1.) 1,10-phenanthroline, n-BuLi / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, HMPA, -78 deg C, 5 min

5: 99 percent / tetrabutylammonium fluoride / hexane / 6 h / Ambient temperature

6: 82 percent / oxalyl chloride, Me₂SO, Et₃N / CH₂Cl₂ / 30 h / -78 °C

7: 97 percent / CH₂Cl₂ / 72 h / Ambient temperature

8: 100 percent / DIBAH / diethyl ether; hexane / 0.58 h / -78 °C

9: 89 percent / oxylal chloride, Me₂SO / CH₂Cl₂ / 0.5 h / -78 °C

With n-butyllithium; 1,10-Phenanthroline; oxalyl dichloride; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In diethyl ether; hexane; dichloromethane;

DOI:10.1021/jo00383a012

upstream raw materials:

(2E,8E)-(4S,6S,7S)-2,4,6-trimethyl-7-(benzyloxy)-2,8,10-undecatrien-1-ol

(2S,4S)-5-<(tert-butyldimethylsilyl)oxy>-2,4-dimethyl-pentanal

(2S,4S)-5-<(tert-butyldimethylsilyl)oxy>-2,4-dimethyl-pentan-1-ol

(3E)-(5S,6S,8S)-9-<(tert-butyldimethylsilyl)oxy>-6,8-dimethyl-1,3-nonadien-5-ol

Downstream raw materials:

(1R,4aS,5S,6S,8S,8aR)-5-Benzyloxy-1,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbaldehyde