(8R,15S)-Dihydroxy-(5Z,9E,11Z,13E)-eicosatetraenoic Acid

Base Information

• Chemical Name: (8R,15S)-Dihydroxy-(5Z,9E,11Z,13E)-eicosatetraenoic Acid
• CAS No.: 80234-64-6
• Molecular Formula: C₂₀H₃₂O₄
• Molecular Weight: 336.472
• Mol file: 80234-64-6.mol

Synonyms:(8R,15S)-dihydroxy-(5Z,9E,11Z,13E)-*eicosatetraen

Chemical Property of (8R,15S)-Dihydroxy-(5Z,9E,11Z,13E)-eicosatetraenoic Acid

Chemical Property:

• PSA: 77.76000
• LogP: 4.15830

Purity/Quality:

(8R,15S)-DIHYDROXY(5Z,9E,11Z,13E)EICOSATETRAENOIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (8R,15S)-Dihydroxy-(5Z,9E,11Z,13E)-eicosatetraenoic Acid

There total 25 articles about (8R,15S)-Dihydroxy-(5Z,9E,11Z,13E)-eicosatetraenoic Acid 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-carboxybutyl)triphenylphosphonium bromide (17814-85-6) → 8(R),15(S) dihydroxy 5Z,9E,11E,13Z eicosatetraenoic acid (77667-08-4,80234-64-6,80234-65-7,80234-66-8,80234-67-9,93292-73-0,104125-26-0,104125-27-1,118758-87-5,125589-73-3,133577-77-2,133577-78-3,133577-79-4,133577-80-7)

Guidance literature:

Multi-step reaction with 12 steps

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

4: aq. acid

5: lead tetraacetate / CH₂Cl₂ / -78 °C

7: 2.) sodium borohydride/ceric chloride / 2.) isopropanol

8: 1) DIPHOS, carbon tetrabromide / 2) triphenylphosphine

9: LiHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide

11: tetrabutylammonium fluoride

12: aq. potassium carbonate

With lead(IV) acetate; sodium tetrahydroborate; ceric chloride; carbon tetrabromide; temephos; tetrabutyl ammonium fluoride; potassium carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;

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

Reference yield:

(4-carboxybutylene)triphenylphosphorane (39968-97-3) → 8(R),15(S) dihydroxy 5Z,9E,11E,13Z eicosatetraenoic acid (77667-08-4,80234-64-6,80234-65-7,80234-66-8,80234-67-9,93292-73-0,104125-26-0,104125-27-1,118758-87-5,125589-73-3,133577-77-2,133577-78-3,133577-79-4,133577-80-7)

Guidance literature:

Multi-step reaction with 11 steps

3: aq. acid

4: lead tetraacetate / CH₂Cl₂ / -78 °C

6: 2.) sodium borohydride/ceric chloride / 2.) isopropanol

7: 1) DIPHOS, carbon tetrabromide / 2) triphenylphosphine

8: LiHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide

10: tetrabutylammonium fluoride

11: aq. potassium carbonate

With lead(IV) acetate; sodium tetrahydroborate; ceric chloride; carbon tetrabromide; temephos; tetrabutyl ammonium fluoride; potassium carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;

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

Reference yield:

[(2E,4E,8Z)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-12-methoxycarbonyl-dodeca-2,4,8-trienyl]-triphenyl-phosphonium; bromide (93292-60-5) → 8(R),15(S) dihydroxy 5Z,9E,11E,13Z eicosatetraenoic acid (77667-08-4,80234-64-6,80234-65-7,80234-66-8,80234-67-9,93292-73-0,104125-26-0,104125-27-1,118758-87-5,125589-73-3,133577-77-2,133577-78-3,133577-79-4,133577-80-7)

Guidance literature:

Multi-step reaction with 4 steps

1: LiHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide

3: tetrabutylammonium fluoride

4: aq. potassium carbonate

With tetrabutyl ammonium fluoride; potassium carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;

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

upstream raw materials:

(5Z,9E,11Z,13E)-(8R,15S)-8,15-Dihydroxy-icosa-5,9,11,13-tetraenoic acid methyl ester

(4-carboxybutyl)triphenylphosphonium bromide

(4-carboxybutylene)triphenylphosphorane

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