(5Z,9E,11E,13E)-(8R,15S)-8,15-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-5,9,11,13-tetraenoic acid methyl ester

Base Information

• Chemical Name: (5Z,9E,11E,13E)-(8R,15S)-8,15-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-5,9,11,13-tetraenoic acid methyl ester
• CAS No.: 93292-70-7
• Molecular Formula: C₅₃H₇₀O₄Si₂
• Molecular Weight: 827.307
• Mol file: 93292-70-7.mol

Synonyms:

Chemical Property of (5Z,9E,11E,13E)-(8R,15S)-8,15-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-5,9,11,13-tetraenoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5Z,9E,11E,13E)-(8R,15S)-8,15-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-5,9,11,13-tetraenoic acid methyl ester

There total 16 articles about (5Z,9E,11E,13E)-(8R,15S)-8,15-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-5,9,11,13-tetraenoic 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:

(4-carboxybutylene)triphenylphosphorane (39968-97-3) → (5Z,9E,11E,13E)-(8R,15S)-8,15-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-5,9,11,13-tetraenoic acid methyl ester (93292-70-7)

Guidance literature:

Multi-step reaction with 6 steps

3: aq. acid

4: lead tetraacetate / CH₂Cl₂ / -78 °C

6: 2.) n-butyllithium / 2.) THF, -100 deg C, then HMPA

With lead(IV) acetate; n-butyllithium; In dichloromethane;

DOI:10.1016/0040-4039(84)80003-9

Reference yield:

(4-carboxybutyl)triphenylphosphonium bromide (17814-85-6) → (5Z,9E,11E,13E)-(8R,15S)-8,15-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-5,9,11,13-tetraenoic acid methyl ester (93292-70-7)

Guidance literature:

Multi-step reaction with 7 steps

1: lithium hexamethyldisilazide (LiHMDS) / tetrahydrofuran; hexamethylphosphoric acid triamide

4: aq. acid

5: lead tetraacetate / CH₂Cl₂ / -78 °C

7: 2.) n-butyllithium / 2.) THF, -100 deg C, then HMPA

With lead(IV) acetate; n-butyllithium; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;

DOI:10.1016/0040-4039(84)80003-9

Reference yield:

(Z)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-oct-5-enoic acid (93292-44-5) → (5Z,9E,11E,13E)-(8R,15S)-8,15-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-5,9,11,13-tetraenoic acid methyl ester (93292-70-7)

Guidance literature:

Multi-step reaction with 5 steps

2: aq. acid

3: lead tetraacetate / CH₂Cl₂ / -78 °C

5: 2.) n-butyllithium / 2.) THF, -100 deg C, then HMPA

With lead(IV) acetate; n-butyllithium; In dichloromethane;

DOI:10.1016/0040-4039(84)80003-9

upstream raw materials:

8(R),15(S),5Z,9,11,13E-diHETE

(5Z,9E)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-11-oxo-undeca-5,9-dienoic acid methyl ester

tert-Butyl-[(S)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hexyloxy]-diphenyl-silane

(4-carboxybutyl)triphenylphosphonium bromide

Downstream raw materials:

8(R),15(S),5Z,9,11,13E-diHETE

Refernces