(2S,5S,6S,9S,10S)-1-benzyloxy-2,5;6,9-diepoxy-10-(methoxymethoxy)tetracosane

Base Information

• Chemical Name: (2S,5S,6S,9S,10S)-1-benzyloxy-2,5;6,9-diepoxy-10-(methoxymethoxy)tetracosane
• CAS No.: 221468-61-7
• Molecular Formula: C₃₃H₅₆O₅
• Molecular Weight: 532.805
• Mol file: 221468-61-7.mol

Synonyms:(2S,5S,6S,9S,10S)-1-benzyloxy-2,5;6,9-diepoxy-10-(methoxymethoxy)tetracosane

Chemical Property of (2S,5S,6S,9S,10S)-1-benzyloxy-2,5;6,9-diepoxy-10-(methoxymethoxy)tetracosane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5S,6S,9S,10S)-1-benzyloxy-2,5;6,9-diepoxy-10-(methoxymethoxy)tetracosane

There total 7 articles about (2S,5S,6S,9S,10S)-1-benzyloxy-2,5;6,9-diepoxy-10-(methoxymethoxy)tetracosane 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: 90.0%

chloromethyl methyl ether (107-30-2) + (2S,5S,6S,9S,10S)-1-benzyloxy-2,5;6,9-diepoxy-10-tetracosanol (221468-04-8) → (2S,5S,6S,9S,10S)-1-benzyloxy-2,5;6,9-diepoxy-10-(methoxymethoxy)tetracosane (221468-61-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 24h;

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

Reference yield:

(5S,6S)-5,6-dihydroxydeca-1,9-diene (221467-95-4) → (2S,5S,6S,9S,10S)-1-benzyloxy-2,5;6,9-diepoxy-10-(methoxymethoxy)tetracosane (221468-61-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 78 percent / t-BuOOH; O₂ / Co(modp)2 / propan-2-ol / 3 h / 60 °C

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

2.2: 71 percent / tetrahydrofuran / 8 h / 0 °C

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

4.1: CuBr*SMe₂ / diethyl ether; various solvent(s) / -78 - 20 °C

5.1: 90 percent / ethyldiisopropylamine / CH₂Cl₂ / 24 h / 20 °C

With tert.-butylhydroperoxide; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; oxygen; sodium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 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 / 5.1: Etherification;

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

Reference yield:

trans-1,5,9-decatriene (39139-91-8,13393-64-1,22146-85-6) → (2S,5S,6S,9S,10S)-1-benzyloxy-2,5;6,9-diepoxy-10-(methoxymethoxy)tetracosane (221468-61-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 57 percent / K₃Fe(CN)6; K₂CO₃; MeSO₂NH₂ / (DHQ)2PHAL; K₂OsO₂(OH)4 / 2-methyl-propan-2-ol; H₂O / 12 h / 0 °C

2.1: 78 percent / t-BuOOH; O₂ / Co(modp)2 / propan-2-ol / 3 h / 60 °C

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

3.2: 71 percent / tetrahydrofuran / 8 h / 0 °C

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

5.1: CuBr*SMe₂ / diethyl ether; various solvent(s) / -78 - 20 °C

6.1: 90 percent / ethyldiisopropylamine / CH₂Cl₂ / 24 h / 20 °C

With tert.-butylhydroperoxide; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; methanesulfonamide; oxygen; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hexacyanoferrate(III); Hydroquinone 1,4-phthalazinediyl diether; potassium dioxotetrahydroxoosmate(VI); Co(modp)2; 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 / 6.1: Etherification;

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

upstream raw materials:

chloromethyl methyl ether

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

trans-1,5,9-decatriene

benzyl bromide