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

Base Information

• Chemical Name: (5S,6R,7S,18R,E)-5,6,7-tris(benzyloxy)-18-methyloxacyclooctadec-3-en-2-one
• CAS No.: 915790-36-2
• Molecular Formula: C₃₉H₅₀O₅
• Molecular Weight: 598.823
• Mol file: 915790-36-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 30 articles about (5S,6R,7S,18R,E)-5,6,7-tris(benzyloxy)-18-methyloxacyclooctadec-3-en-2-one 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: 18.0%

(4R,5S,6R,17S,E)-4,5,6-tris(benzyloxy)-17-hydroxyoctadec-2-enal (915790-34-0) → (5S,6R,7S,18R,E)-5,6,7-tris(benzyloxy)-18-methyloxacyclooctadec-3-en-2-one (915790-36-2)

Guidance literature:

(4R,5S,6R,17S,E)-4,5,6-tris(benzyloxy)-17-hydroxyoctadec-2-enal; With potassium cyanide; manganese(IV) oxide; at 20 ℃; for 48h;

With dmap; In toluene; for 0.25h; Heating;

DOI:10.1021/ol0620287

Reference yield:

C46H53Cl3O7 → (5S,6R,7S,18R,E)-5,6,7-tris(benzyloxy)-18-methyloxacyclooctadec-3-en-2-one (915790-36-2)

Guidance literature:

With dmap; In toluene; at 90 ℃; for 10h; Inert atmosphere;

DOI:10.1080/00397911.2018.1458241

Reference yield:

8-Bromo-1-octene (2695-48-9) → (5S,6R,7S,18R,E)-5,6,7-tris(benzyloxy)-18-methyloxacyclooctadec-3-en-2-one (915790-36-2)

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: MnO₂; KCN / 48 h / 20 °C

16.2: 18 percent / DMAP / toluene / 0.25 h / Heating

With 1H-imidazole; dmap; potassium cyanide; manganese(IV) oxide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; 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; acetone; 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

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

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

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

Downstream raw materials:

(+)-aspicilin

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.