(R)-1-benzyl-5-<4-(2-methyl-1,3-dioxolan-2-yl)-1-((benzyloxy)carbonyl)butylidene>proline tert-butyl ester

Base Information

• Chemical Name: (R)-1-benzyl-5-<4-(2-methyl-1,3-dioxolan-2-yl)-1-((benzyloxy)carbonyl)butylidene>proline tert-butyl ester
• CAS No.: 96998-26-4
• Molecular Formula: C₃₂H₄₁NO₆
• Molecular Weight: 535.681
• Mol file: 96998-26-4.mol

Synonyms:(R)-1-benzyl-5-<4-(2-methyl-1,3-dioxolan-2-yl)-1-((benzyloxy)carbonyl)butylidene>proline tert-butyl ester

Chemical Property of (R)-1-benzyl-5-<4-(2-methyl-1,3-dioxolan-2-yl)-1-((benzyloxy)carbonyl)butylidene>proline tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-benzyl-5-<4-(2-methyl-1,3-dioxolan-2-yl)-1-((benzyloxy)carbonyl)butylidene>proline tert-butyl ester

There total 7 articles about (R)-1-benzyl-5-<4-(2-methyl-1,3-dioxolan-2-yl)-1-((benzyloxy)carbonyl)butylidene>proline tert-butyl ester 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%

(R)-1-benzyl-5-thioxoproline tert-butyl ester (90741-32-5) + benzyl (+/-)-5-(2-methyl-1,3-dioxolan-2-yl)-2-<((trifluoromethyl)sulfonyl)oxy>pentanoate (96929-76-9) → (R)-1-benzyl-5-<4-(2-methyl-1,3-dioxolan-2-yl)-1-((benzyloxy)carbonyl)butylidene>proline tert-butyl ester (96998-26-4)

Guidance literature:

With N-methylcyclohexylamine; triphenylphosphine; In dichloromethane; at -20 - 0 ℃; for 6h;

DOI:10.1021/jm00147a032

Reference yield:

ethylene-cetal de la bromo-5 pentanone-2 (24400-75-7) → (R)-1-benzyl-5-<4-(2-methyl-1,3-dioxolan-2-yl)-1-((benzyloxy)carbonyl)butylidene>proline tert-butyl ester (96998-26-4)

Guidance literature:

Multi-step reaction with 4 steps

2: Et₃N, H₂ / 5percent Pt/C / ethyl acetate / 0.27 h / 2585.7 Torr

3: 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 1) 0 deg C, 30 min, 2) r.t., 1 h

4: 2) Ph₃P, N-methylpiperidine / 1) CH₃CN, 0 deg C, 30 min then r.t., 19 h 2) CH₂Cl₂, 0 deg C, 4 h

With N-methylcyclohexylamine; 2,6-di-tert-butyl-4-methylpyridine; hydrogen; triethylamine; triphenylphosphine; platinum on activated charcoal; In dichloromethane; ethyl acetate;

DOI:10.1021/ja00328a040

Reference yield:

dibenzyl oxalate (7579-36-4) → (R)-1-benzyl-5-<4-(2-methyl-1,3-dioxolan-2-yl)-1-((benzyloxy)carbonyl)butylidene>proline tert-butyl ester (96998-26-4)

Guidance literature:

Multi-step reaction with 4 steps

2: Et₃N, H₂ / 5percent Pt/C / ethyl acetate / 0.27 h / 2585.7 Torr

3: 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 1) 0 deg C, 30 min, 2) r.t., 1 h

4: 2) Ph₃P, N-methylpiperidine / 1) CH₃CN, 0 deg C, 30 min then r.t., 19 h 2) CH₂Cl₂, 0 deg C, 4 h

With N-methylcyclohexylamine; 2,6-di-tert-butyl-4-methylpyridine; hydrogen; triethylamine; triphenylphosphine; platinum on activated charcoal; In dichloromethane; ethyl acetate;

DOI:10.1021/ja00328a040

upstream raw materials:

(R)-1-benzyl-5-thioxoproline tert-butyl ester

benzyl (+/-)-5-(2-methyl-1,3-dioxolan-2-yl)-2-<((trifluoromethyl)sulfonyl)oxy>pentanoate

ethylene-cetal de la bromo-5 pentanone-2

dibenzyl oxalate

Downstream raw materials:

(2R)-cis-1-benzyl-5-<4-(2-methyl-1,3-dioxolan-2-yl)butyl>proline tert-butyl ester