(2E,8E,10E,12E)-(4S,6S,7S)-7,14-Bis(benzyloxy)-2,4,6,12-tetramethyl-2,8,10,12-tetradecatetraenal

Base Information

• Chemical Name: (2E,8E,10E,12E)-(4S,6S,7S)-7,14-Bis(benzyloxy)-2,4,6,12-tetramethyl-2,8,10,12-tetradecatetraenal
• CAS No.: 125590-09-2
• Molecular Formula: C₃₂H₄₀O₃
• Molecular Weight: 472.668
• Mol file: 125590-09-2.mol

Synonyms:(2E,8E,10E,12E)-(4S,6S,7S)-7,14-Bis(benzyloxy)-2,4,6,12-tetramethyl-2,8,10,12-tetradecatetraenal

Chemical Property of (2E,8E,10E,12E)-(4S,6S,7S)-7,14-Bis(benzyloxy)-2,4,6,12-tetramethyl-2,8,10,12-tetradecatetraenal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,8E,10E,12E)-(4S,6S,7S)-7,14-Bis(benzyloxy)-2,4,6,12-tetramethyl-2,8,10,12-tetradecatetraenal

There total 22 articles about (2E,8E,10E,12E)-(4S,6S,7S)-7,14-Bis(benzyloxy)-2,4,6,12-tetramethyl-2,8,10,12-tetradecatetraenal 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:

(2E,8E,10E,12E)-(4S,6S,7S)-7,14-Bis(benzyloxy)-2,4,6,12-tetramethyl-2,8,10,12-tetradecatetraen-1-ol (125590-08-1) → (2E,8E,10E,12E)-(4S,6S,7S)-7,14-Bis(benzyloxy)-2,4,6,12-tetramethyl-2,8,10,12-tetradecatetraenal (125590-09-2)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃;

DOI:10.1021/jo00295a030

Reference yield:

(2E,8E,10E,12E)-(4R,6R)-7,14-Bis-benzyloxy-2,4,6,12-tetramethyl-tetradeca-2,8,10,12-tetraen-1-ol (101376-84-5,101469-64-1,125590-08-1) → (2E,8E,10E,12E)-(4R,6R)-7,14-Bis-benzyloxy-2,4,6,12-tetramethyl-tetradeca-2,8,10,12-tetraenal (101376-85-6,101469-65-2,125590-09-2)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; Yield given;

DOI:10.1021/jo00359a060

Reference yield:

(E)-4-(benzyloxy)-2-methylbut-2-en-1-ol (70238-41-4) → (2E,8E,10E,12E)-(4R,6R)-7,14-Bis-benzyloxy-2,4,6,12-tetramethyl-tetradeca-2,8,10,12-tetraenal (101376-85-6,101469-65-2,125590-09-2)

Guidance literature:

Multi-step reaction with 12 steps

1: (COCl)2, Me₂SO, Et₃N / CH₂Cl₂

2: -78 °C

3: Bu₄NF / tetrahydrofuran / 0 - 23 °C

4: n-BuLi / tetrahydrofuran / -78 °C

5: tetrahydrofuran / -40 °C

6: red-Al / diethyl ether / 0 - 23 °C

7: n-BuLi, HMPA / tetrahydrofuran

8: Bu₄NF / tetrahydrofuran / 23 °C

9: (COCl)2, Me₂SO, Et₃N / CH₂Cl₂

10: CH₂Cl₂

11: DIBAH / diethyl ether / -78 °C

12: (COCl)2, Me₂SO, Et₃N / CH₂Cl₂

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo00359a060

upstream raw materials:

(2E,8E,10E,12E)-(4S,6S,7S)-7,14-Bis(benzyloxy)-2,4,6,12-tetramethyl-2,8,10,12-tetradecatetraen-1-ol

(2E,4E,6E)-(8S,9S,11S)-12-<(tert-Butyldimethylsilyl)oxy>-3,9,11-trimethyl-1-(benzyloxy)-2,4,6-dodecatrien-8-ol

(2E,4E)-(9S,11S)-12-<(tert-Butyldimethylsilyl)oxy>-3,9,11-trimethyl-1-(benzyloxy)-2,4-dodecadien-6-yn-8-one

(6E,8E,10E)-(2S,4S,5S)-5,12-Bis(benzyloxy)-2,4,10-trimethyl-6,8,10-dodecatrienal

Downstream raw materials:

(3S,4S,4aS,5S,7S,8S,8aS)-8-(Benzyloxy)-4,5,7-trimethyl-3-<(E)-3-(benzyloxy)-1-methyl-1-propenyl>-3,4,4a,5,6,7,8,8a-octahydronaphthalene-4-carboxaldehyde