(8R,15S)-8,15-dihydroxyicosa-5,9,11,13-tetraenoic acid

Base Information

• Chemical Name: (8R,15S)-8,15-dihydroxyicosa-5,9,11,13-tetraenoic acid
• CAS No.: 80234-67-9
• Molecular Formula: C₂₀H₃₂O₄
• Molecular Weight: 336.472
• DSSTox Substance ID: DTXSID80425010
• Mol file: 80234-67-9.mol

Synonyms:(8R,15S)-8,15-dihydroxyicosa-5,9,11,13-tetraenoic acid;80234-67-9;AC1O7M0F;CBiol_001849;DTXSID80425010;Bio1_000135;Bio1_000624;Bio1_001113

Chemical Property of (8R,15S)-8,15-dihydroxyicosa-5,9,11,13-tetraenoic acid

Chemical Property:

• PSA: 77.76000
• LogP: 4.15830
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 14
• Exact Mass: 336.23005950
• Heavy Atom Count: 24
• Complexity: 421

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=CC=CC=CC(CC=CCCCC(=O)O)O)O
• Isomeric SMILES: CCCCC[C@@H](C=CC=CC=C[C@@H](CC=CCCCC(=O)O)O)O

Technology Process of (8R,15S)-8,15-dihydroxyicosa-5,9,11,13-tetraenoic acid

There total 34 articles about (8R,15S)-8,15-dihydroxyicosa-5,9,11,13-tetraenoic 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,11E,13Z)-(8R,15S)-8,15-Dihydroxy-icosa-5,9,11,13-tetraenoic acid methyl ester

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

(4-carboxybutyl)triphenylphosphonium bromide

(S)-2-(tert-butyldiphenylsilyloxy)heptanal

Downstream raw materials:

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

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

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

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