tert-butyl 4-[(1R,2E)-1-benzoyloxyhexadec-2-enyl]-2,2-dimethyloxazolidine-3-carboxylate

Base Information

• Chemical Name: tert-butyl 4-[(1R,2E)-1-benzoyloxyhexadec-2-enyl]-2,2-dimethyloxazolidine-3-carboxylate
• CAS No.: 263558-18-5
• Molecular Formula: C₃₃H₅₃NO₅
• Molecular Weight: 543.788
• Mol file: 263558-18-5.mol

Synonyms:tert-butyl 4-[(1R,2E)-1-benzoyloxyhexadec-2-enyl]-2,2-dimethyloxazolidine-3-carboxylate

Chemical Property of tert-butyl 4-[(1R,2E)-1-benzoyloxyhexadec-2-enyl]-2,2-dimethyloxazolidine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 4-[(1R,2E)-1-benzoyloxyhexadec-2-enyl]-2,2-dimethyloxazolidine-3-carboxylate

There total 5 articles about tert-butyl 4-[(1R,2E)-1-benzoyloxyhexadec-2-enyl]-2,2-dimethyloxazolidine-3-carboxylate 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: 84.0%

benzoyl chloride (98-88-4) + tert-butyl (4S)-4-[(1R,2E)-1-hydroxy-2-hexadecenyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (115464-03-4) → tert-butyl 4-[(1R,2E)-1-benzoyloxyhexadec-2-enyl]-2,2-dimethyloxazolidine-3-carboxylate (263558-18-5)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; for 20h;

DOI:10.1002/ejoc.201500025

Reference yield: 72.0%

benzoic acid (65-85-0,8013-63-6) + tert-butyl (4S)-4-[(1S,2E)-1-hydroxy-2-hexadecenyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (115464-04-5) → tert-butyl 4-[(1R,2E)-1-benzoyloxyhexadec-2-enyl]-2,2-dimethyloxazolidine-3-carboxylate (263558-18-5)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; for 36h;

DOI:10.1039/b002104k

Reference yield:

tert-butyl (S)-4-((R)-1-hydroxyallyl)-2,2-dimethyloxazolidine-3-carboxylate (114301-34-7,114301-35-8,117487-60-2,122709-37-9,117487-58-8) → tert-butyl 4-[(1R,2E)-1-benzoyloxyhexadec-2-enyl]-2,2-dimethyloxazolidine-3-carboxylate (263558-18-5)

Guidance literature:

Multi-step reaction with 2 steps

1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; acetic acid / dichloromethane / Inert atmosphere; Reflux

2: pyridine; dmap / dichloromethane / 20 h / 20 °C

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; acetic acid; In dichloromethane;

DOI:10.1002/ejoc.201500025

upstream raw materials:

benzoyl chloride

tert-butyl (4S)-4-[(1R,2E)-1-hydroxy-2-hexadecenyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

benzoic acid

tert-butyl (4S)-4-[(1S,2E)-1-hydroxy-2-hexadecenyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Downstream raw materials:

N-tert-butyloxycarbonylsphingosine

N-(tert-butoxycarbonyl)-3-O-benzoyl-D-erythro-sphingosine

glucosylceramide

3-O-benzoyl-1-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N-stearoyl-D-erythro-sphingosine