(2E,8E,10E,12E)-(4S,6S,7S)-Methyl 7,14-bis(benzyloxy)-2,4,6,12-tetramethyltetradeca-2,8,10,12-tetraenoate

Base Information

• Chemical Name: (2E,8E,10E,12E)-(4S,6S,7S)-Methyl 7,14-bis(benzyloxy)-2,4,6,12-tetramethyltetradeca-2,8,10,12-tetraenoate
• CAS No.: 125590-07-0
• Molecular Formula: C₃₃H₄₂O₄
• Molecular Weight: 502.694
• Mol file: 125590-07-0.mol

Synonyms:(2E,8E,10E,12E)-(4S,6S,7S)-Methyl 7,14-bis(benzyloxy)-2,4,6,12-tetramethyltetradeca-2,8,10,12-tetraenoate

Chemical Property of (2E,8E,10E,12E)-(4S,6S,7S)-Methyl 7,14-bis(benzyloxy)-2,4,6,12-tetramethyltetradeca-2,8,10,12-tetraenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,8E,10E,12E)-(4S,6S,7S)-Methyl 7,14-bis(benzyloxy)-2,4,6,12-tetramethyltetradeca-2,8,10,12-tetraenoate

There total 17 articles about (2E,8E,10E,12E)-(4S,6S,7S)-Methyl 7,14-bis(benzyloxy)-2,4,6,12-tetramethyltetradeca-2,8,10,12-tetraenoate 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:

(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-tetraenoic acid methyl ester (101376-83-4,101470-18-2,125590-07-0)

Guidance literature:

Multi-step reaction with 10 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

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

DOI:10.1021/jo00359a060

Reference yield:

benzyloxyacetoaldehyde (60656-87-3) → (2E,8E,10E,12E)-(4R,6R)-7,14-Bis-benzyloxy-2,4,6,12-tetramethyl-tetradeca-2,8,10,12-tetraenoic acid methyl ester (101376-83-4,101470-18-2,125590-07-0)

Guidance literature:

Multi-step reaction with 12 steps

1: CH₂Cl₂

2: DIBAH / diethyl ether / -78 °C

3: (COCl)2, Me₂SO, Et₃N / CH₂Cl₂

4: -78 °C

5: Bu₄NF / tetrahydrofuran / 0 - 23 °C

6: n-BuLi / tetrahydrofuran / -78 °C

7: tetrahydrofuran / -40 °C

8: red-Al / diethyl ether / 0 - 23 °C

9: n-BuLi, HMPA / tetrahydrofuran

10: Bu₄NF / tetrahydrofuran / 23 °C

11: (COCl)2, Me₂SO, Et₃N / CH₂Cl₂

12: 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

Reference yield:

(E)-4-(benzyloxy)-2-methylbut-2-enal (101376-74-3) → (2E,8E,10E,12E)-(4R,6R)-7,14-Bis-benzyloxy-2,4,6,12-tetramethyl-tetradeca-2,8,10,12-tetraenoic acid methyl ester (101376-83-4,101470-18-2,125590-07-0)

Guidance literature:

Multi-step reaction with 9 steps

1: -78 °C

2: Bu₄NF / tetrahydrofuran / 0 - 23 °C

3: n-BuLi / tetrahydrofuran / -78 °C

4: tetrahydrofuran / -40 °C

5: red-Al / diethyl ether / 0 - 23 °C

6: n-BuLi, HMPA / tetrahydrofuran

7: Bu₄NF / tetrahydrofuran / 23 °C

8: (COCl)2, Me₂SO, Et₃N / CH₂Cl₂

9: CH₂Cl₂

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

DOI:10.1021/jo00359a060

upstream raw materials:

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

methyl 2-(triphenylphosphoranylidene)propionate

(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

Downstream 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

Methyl (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-carboxylate

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

(2E,8E,10E,12E)-(4R,6R)-7,14-Bis-benzyloxy-2,4,6,12-tetramethyl-tetradeca-2,8,10,12-tetraen-1-ol