(5S,6E)-5-methyl-2-[(1R,2E)-1-methyl-5-(benzyloxy)-2-pentenyl]-3-oxo-9-(benzyloxy)-6-nonenoic acid ethyl ester

Base Information

• Chemical Name: (5S,6E)-5-methyl-2-[(1R,2E)-1-methyl-5-(benzyloxy)-2-pentenyl]-3-oxo-9-(benzyloxy)-6-nonenoic acid ethyl ester
• CAS No.: 214484-04-5
• Molecular Formula: C₃₂H₄₂O₅
• Molecular Weight: 506.682
• Mol file: 214484-04-5.mol

Synonyms:(5S,6E)-5-methyl-2-[(1R,2E)-1-methyl-5-(benzyloxy)-2-pentenyl]-3-oxo-9-(benzyloxy)-6-nonenoic acid ethyl ester

Chemical Property of (5S,6E)-5-methyl-2-[(1R,2E)-1-methyl-5-(benzyloxy)-2-pentenyl]-3-oxo-9-(benzyloxy)-6-nonenoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6E)-5-methyl-2-[(1R,2E)-1-methyl-5-(benzyloxy)-2-pentenyl]-3-oxo-9-(benzyloxy)-6-nonenoic acid ethyl ester

There total 4 articles about (5S,6E)-5-methyl-2-[(1R,2E)-1-methyl-5-(benzyloxy)-2-pentenyl]-3-oxo-9-(benzyloxy)-6-nonenoic acid ethyl 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: 84.0%

(3S,4E)-3-methyl-7-benzyloxy-4-heptenoic acid ethyl ester (214483-92-8) → (5S,6E)-5-methyl-2-[(1R,2E)-1-methyl-5-(benzyloxy)-2-pentenyl]-3-oxo-9-(benzyloxy)-6-nonenoic acid ethyl ester (214484-04-5)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; lithium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 4.5h;

DOI:10.1021/jo981181e

Reference yield:

(S,E)-1-(benzyloxy)hex-4-en-3-ol (214483-91-7) → (5S,6E)-5-methyl-2-[(1R,2E)-1-methyl-5-(benzyloxy)-2-pentenyl]-3-oxo-9-(benzyloxy)-6-nonenoic acid ethyl ester (214484-04-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / propionic acid / 26 h / 145 °C

2: 84 percent / HMDS; TMEDA; n-BuLi / tetrahydrofuran / 0 °C

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; propionic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran;

DOI:10.1016/S0040-4020(02)00050-9

Reference yield:

(3S)-1-benzyloxy-4-hexyn-3-ol (214483-90-6) → (5S,6E)-5-methyl-2-[(1R,2E)-1-methyl-5-(benzyloxy)-2-pentenyl]-3-oxo-9-(benzyloxy)-6-nonenoic acid ethyl ester (214484-04-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / LAH / tetrahydrofuran / 4 h / Heating

2: 92 percent / propionic acid / 26 h / 145 °C

3: 84 percent / HMDS; TMEDA; n-BuLi / tetrahydrofuran / 0 °C

With lithium aluminium tetrahydride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; propionic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran;

DOI:10.1016/S0040-4020(02)00050-9

upstream raw materials:

(3S,4E)-3-methyl-7-benzyloxy-4-heptenoic acid ethyl ester

(S,E)-1-(benzyloxy)hex-4-en-3-ol

(3S)-1-benzyloxy-4-hexyn-3-ol

(S)-(2-phenylmethoxyethyl)oxirane

Downstream raw materials:

(3E,5S,9S,10E)-5,9-dimethyl-1,13-bis(benzyloxy)-3,10-tridecadien-7-one

(3S,4S,5S,9S,10S,11S)-1,13-bis(benzyloxy)-5,9-dimethyl-3,4,10,11-tetrahydroxytridecane-7-one

C₃₅H₄₈O₈Si

C₃₅H₄₈O₈Si