(4R,5S,6R,17S,E)-4,5,6-tris(benzyloxy)-17-hydroxyoctadec-2-enoic acid

Base Information

• Chemical Name: (4R,5S,6R,17S,E)-4,5,6-tris(benzyloxy)-17-hydroxyoctadec-2-enoic acid
• CAS No.: 915790-35-1
• Molecular Formula: C₃₉H₅₂O₆
• Molecular Weight: 616.838
• Mol file: 915790-35-1.mol

Synonyms:(4R,5S,6R,17S,E)-4,5,6-tris(benzyloxy)-17-hydroxyoctadec-2-enoic acid

Chemical Property of (4R,5S,6R,17S,E)-4,5,6-tris(benzyloxy)-17-hydroxyoctadec-2-enoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S,6R,17S,E)-4,5,6-tris(benzyloxy)-17-hydroxyoctadec-2-enoic acid

There total 28 articles about (4R,5S,6R,17S,E)-4,5,6-tris(benzyloxy)-17-hydroxyoctadec-2-enoic 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: 96.0%

(4R,5S,6R,17S,E)-4,5,6-tris(benzyloxy)-17-hydroxyoctadec-2-enal (915790-34-0) → (4R,5S,6R,17S,E)-4,5,6-tris(benzyloxy)-17-hydroxyoctadec-2-enoic acid (915790-35-1)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; at 20 ℃; for 0.5h;

DOI:10.1021/ol0620287

Reference yield: 89.0%

(4R,5S,6R,17S,E)-methyl 4,5,6-tris(benzyloxy)-17-(tert-butyldiphenylsilyloxy)octadec-2-enoate → (4R,5S,6R,17S,E)-4,5,6-tris(benzyloxy)-17-hydroxyoctadec-2-enoic acid (915790-35-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1080/00397911.2018.1458241

Reference yield:

8-Bromo-1-octene (2695-48-9) → (4R,5S,6R,17S,E)-4,5,6-tris(benzyloxy)-17-hydroxyoctadec-2-enoic acid (915790-35-1)

Guidance literature:

Multi-step reaction with 16 steps

1.1: Mg; dibromoethane / tetrahydrofuran / Heating

1.2: 89 percent / CuCN / tetrahydrofuran / 5 h / -15 - 20 °C

2.1: 99 percent / imidazole; DMAP / CH₂Cl₂ / 5 h / 20 °C

3.1: 9-BBN-H / tetrahydrofuran / 4 h / Heating

3.2: 90 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 12 h / 20 °C

4.1: 92 percent / CBr₄; Ph₃P / CH₂Cl₂ / 24 h / 20 °C

5.1: Mg; dibromoethane / tetrahydrofuran / 4 h / Heating

5.2: CuBr*Me₂S / tetrahydrofuran / 7 h / -25 - 20 °C

6.1: 89 percent / triflic acid / CH₂Cl₂; hexane / 48 h / 20 °C

7.1: 99 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

8.1: 89 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

9.1: 69 percent / SnCl₄ / CH₂Cl₂ / 0.5 h / -78 °C

10.1: 99 percent / LiAlH₄ / tetrahydrofuran / 3 h / Heating

11.1: 79 percent / TBAI; NaH / tetrahydrofuran / 12 h / 0 °C

12.1: 69 percent / ZnCl₂*OEt₂ / CH₂Cl₂; diethyl ether / 72 h / Heating

13.1: O₂ / CH₂Cl₂; methanol / 0.42 h / -78 °C

13.2: 88 percent / NaBH₄ / CH₂Cl₂; methanol / -78 - 0 °C

14.1: 99 percent / TBAF / tetrahydrofuran / 5 h / Heating

15.1: 65 percent / PTSA / acetone / 4 h / 20 - 40 °C

16.1: 96 percent / 2-methyl-but-2-ene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 0.5 h / 20 °C

With 1H-imidazole; dmap; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; 2-methyl-but-2-ene; zinc chloride diethyl ether; 1,1-Dibromoethane; carbon tetrabromide; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; oxygen; tin(IV) chloride; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; magnesium; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetone; tert-butyl alcohol; 12.1: Sakurai reaction;

DOI:10.1021/ol0620287

upstream raw materials:

(4R,5S,6R,17S,E)-4,5,6-tris(benzyloxy)-17-hydroxyoctadec-2-enal

(S)-tert-butyldiphenyl(undec-10-en-2-yloxy)silane

(S)-10-(tert-butyldiphenylsilyloxy)undecan-1-ol

(S)-(11-bromoundecan-2-yloxy)(tert-butyl)diphenylsilane

Downstream raw materials:

(+)-aspicilin

(5S,6R,7S,18R,E)-5,6,7-tris(benzyloxy)-18-methyloxacyclooctadec-3-en-2-one

Refernces

• 1、 Dubost, Christophe,Marko, Istvan E.,Ryckmans, Thomas. "A concise total synthesis of the lichen macrolide (+)-aspicilin". . p. 5137 - 5140. Retrieved 2007/10/03.