(6E,11E)-(9R,10S,13S)-9,13-Bis-benzyloxy-5-oxo-10-vinyl-octadeca-6,11-dienoic acid methyl ester

Base Information

• Chemical Name: (6E,11E)-(9R,10S,13S)-9,13-Bis-benzyloxy-5-oxo-10-vinyl-octadeca-6,11-dienoic acid methyl ester
• CAS No.: 159326-26-8
• Molecular Formula: C₃₅H₄₆O₅
• Molecular Weight: 546.747
• Mol file: 159326-26-8.mol

Synonyms:(6E,11E)-(9R,10S,13S)-9,13-Bis-benzyloxy-5-oxo-10-vinyl-octadeca-6,11-dienoic acid methyl ester

Chemical Property of (6E,11E)-(9R,10S,13S)-9,13-Bis-benzyloxy-5-oxo-10-vinyl-octadeca-6,11-dienoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6E,11E)-(9R,10S,13S)-9,13-Bis-benzyloxy-5-oxo-10-vinyl-octadeca-6,11-dienoic acid methyl ester

There total 1 articles about (6E,11E)-(9R,10S,13S)-9,13-Bis-benzyloxy-5-oxo-10-vinyl-octadeca-6,11-dienoic acid methyl ester 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: 96.0%

(E)-(3R,4S,7S)-3,7-Bis-benzyloxy-4-vinyl-dodec-5-enal (137759-68-3) + diethyl [5-(methoxycarbonyl)-2-oxopentyl]phosphonate → (6E,11E)-(9R,10S,13S)-9,13-Bis-benzyloxy-5-oxo-10-vinyl-octadeca-6,11-dienoic acid methyl ester (159326-26-8)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; 1.) 25 deg C; 2.) -70 deg C;

DOI:10.1016/S0040-4039(00)77275-3

Reference yield: 61.0%

diiodomethane (75-11-6) + (6E,11E)-(9R,10S,13S)-9,13-Bis-benzyloxy-5-oxo-10-vinyl-octadeca-6,11-dienoic acid methyl ester (159326-26-8) → (6E,11E)-(9R,10S,13S)-9,13-Bis-benzyloxy-5-methylene-10-vinyl-octadeca-6,11-dienoic acid methyl ester (159326-27-9)

Guidance literature:

With titanium tetrachloride; zinc; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)77275-3

Reference yield:

(6E,11E)-(9R,10S,13S)-9,13-Bis-benzyloxy-5-oxo-10-vinyl-octadeca-6,11-dienoic acid methyl ester (159326-26-8) → 4-[(1R,2R,3aS,7aS)-2-Benzyloxy-1-((E)-(S)-3-benzyloxy-oct-1-enyl)-2,3,3a,6,7,7a-hexahydro-1H-inden-5-yl]-butyric acid

Guidance literature:

Multi-step reaction with 3 steps

1: 61 percent / TiCl₄, Zn / tetrahydrofuran

2: various solvent(s) / 5 h / 150 °C

3: NaOH / methanol

With sodium hydroxide; titanium tetrachloride; zinc; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4039(00)77275-3

upstream raw materials:

(E)-(3R,4S,7S)-3,7-Bis-benzyloxy-4-vinyl-dodec-5-enal

Downstream raw materials:

(6E,11E)-(9R,10S,13S)-9,13-Bis-benzyloxy-5-methylene-10-vinyl-octadeca-6,11-dienoic acid methyl ester

4-[(1R,2R,3aS,7aS)-2-Benzyloxy-1-((E)-(S)-3-benzyloxy-oct-1-enyl)-2,3,3a,6,7,7a-hexahydro-1H-inden-5-yl]-butyric acid methyl ester