(2R,5R,6R,9R,10R)-1-benzyloxy-2,5;6,9-diepoxy-10-tetracosanol

Base Information

• Chemical Name: (2R,5R,6R,9R,10R)-1-benzyloxy-2,5;6,9-diepoxy-10-tetracosanol
• CAS No.: 261617-87-2
• Molecular Formula: C₃₁H₅₂O₄
• Molecular Weight: 488.751
• Mol file: 261617-87-2.mol

Synonyms:(2R,5R,6R,9R,10R)-1-benzyloxy-2,5;6,9-diepoxy-10-tetracosanol

Chemical Property of (2R,5R,6R,9R,10R)-1-benzyloxy-2,5;6,9-diepoxy-10-tetracosanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5R,6R,9R,10R)-1-benzyloxy-2,5;6,9-diepoxy-10-tetracosanol

There total 8 articles about (2R,5R,6R,9R,10R)-1-benzyloxy-2,5;6,9-diepoxy-10-tetracosanol 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:

trans-1,5,9-decatriene (39139-91-8,13393-64-1,22146-85-6) → (2R,5R,6R,9R,10R)-1-benzyloxy-2,5;6,9-diepoxy-10-tetracosanol (261617-87-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 59 percent / K₃Fe(CN)6; K₂CO₃; MeSO₂NH₂ / (DHQD)2PHAL; K₂OsO₂(OH)4 / 2-methyl-propan-2-ol; H₂O / 12 h / 0 °C

2.1: 80 percent / t-BuOOH; O₂ / Co(modp)2 / propan-2-ol / 3 h / 60 °C

3.1: NaH / tetrahydrofuran / 1 h / 0 °C

3.2: 64 percent / tetrahydrofuran / 8 h / 0 °C

4.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

5.1: diethyl ether; tetrahydrofuran / -78 - 20 °C

With tert.-butylhydroperoxide; oxalyl dichloride; methanesulfonamide; oxygen; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; potassium hexacyanoferrate(III); potassium dioxotetrahydroxoosmate(VI); Co(modp)2; 1,4-bis(9-O-dihydroquinidine)phthalazine; In tetrahydrofuran; diethyl ether; dichloromethane; water; isopropyl alcohol; tert-butyl alcohol; 1.1: Sharpless asymmetric dihydroxylation / 2.1: Oxidation / 3.1: deprotonation / 3.2: Etherification / 4.1: Swern oxidation / 5.1: Grignard reaction;

DOI:10.1002/(SICI)1099-0690(200001)2000:2<349::AID-EJOC349>3.0.CO;2-J

Reference yield:

(5R,6R)-5,6-dihydroxydeca-1,9-diene (203715-36-0) → (2R,5R,6R,9R,10R)-1-benzyloxy-2,5;6,9-diepoxy-10-tetracosanol (261617-87-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 80 percent / t-BuOOH; O₂ / Co(modp)2 / propan-2-ol / 3 h / 60 °C

2.1: NaH / tetrahydrofuran / 1 h / 0 °C

2.2: 64 percent / tetrahydrofuran / 8 h / 0 °C

3.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

4.1: diethyl ether; tetrahydrofuran / -78 - 20 °C

With tert.-butylhydroperoxide; oxalyl dichloride; oxygen; sodium hydride; dimethyl sulfoxide; triethylamine; Co(modp)2; In tetrahydrofuran; diethyl ether; dichloromethane; isopropyl alcohol; 1.1: Oxidation / 2.1: deprotonation / 2.2: Etherification / 3.1: Swern oxidation / 4.1: Grignard reaction;

DOI:10.1002/(SICI)1099-0690(200001)2000:2<349::AID-EJOC349>3.0.CO;2-J

Reference yield:

(2R,5R,6R,9R)-1-benzyloxy-2,5;6,9-diepoxy-10-tetracosanone (261617-85-0) → (2R,5R,6R,9R,10R)-1-benzyloxy-2,5;6,9-diepoxy-10-tetracosanol (261617-87-2) + (2R,5R,6R,9R,10S)-1-benzyloxy-2,5;6,9-diepoxy-10-tetracosanol

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1002/(SICI)1099-0690(200001)2000:2<349::AID-EJOC349>3.0.CO;2-J

upstream raw materials:

n-tetradecylmagnesium chloride

(all-R)-5'-(5''-Benzyloxymethyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-carbaldehyde

(2R,5R,6R,9R)-1-benzyloxy-2,5;6,9-diepoxy-10-tetracosanone

trans-1,5,9-decatriene