1-(Benzyloxycarbonyl)-L-proline benzyl ester

Base Information

• Chemical Name: 1-(Benzyloxycarbonyl)-L-proline benzyl ester
• CAS No.: 124980-30-9
• Molecular Formula: C₂₀H₂₁NO₄
• Molecular Weight: 339.391
• DSSTox Substance ID: DTXSID801173125
• Nikkaji Number: J763.939B
• Mol file: 124980-30-9.mol

Synonyms:SCHEMBL7326760;DTXSID801173125;1-(Benzyloxycarbonyl)-L-proline benzyl ester;1,2-Pyrrolidinedicarboxylic acid, bis(phenylmethyl) ester, (2S)-;124980-30-9

Chemical Property of 1-(Benzyloxycarbonyl)-L-proline benzyl ester

Chemical Property:

• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 339.14705815
• Heavy Atom Count: 25
• Complexity: 441

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC(N(C1)C(=O)OCC2=CC=CC=C2)C(=O)OCC3=CC=CC=C3
• Isomeric SMILES: C1C[C@H](N(C1)C(=O)OCC2=CC=CC=C2)C(=O)OCC3=CC=CC=C3

Technology Process of 1-(Benzyloxycarbonyl)-L-proline benzyl ester

There total 9 articles about 1-(Benzyloxycarbonyl)-L-proline benzyl 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: 83.0%

benzyl L-<(2-benzyloxycarbonyl)amino>-5-hydroxypentanoate (167319-89-3) → N-carbobenzoxy-L-proline phenylmethyl ester (124980-30-9)

Guidance literature:

With sodium hydride; In tetrahydrofuran; Ambient temperature;

DOI:10.1246/cl.1996.621

Reference yield: 82.0%

(S)-benzyloxycarbonyl-proline acid chloride (61350-60-5,61350-62-7,89705-40-8,106709-50-6) + benzyl alcohol (100-51-6,185532-71-2) → N-carbobenzoxy-L-proline phenylmethyl ester (124980-30-9)

Guidance literature:

With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate; In acetonitrile; at 0 - 5 ℃; for 1h;

DOI:10.1016/j.tet.2007.08.117

Reference yield: 81.0%

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride (16652-71-4) → N-carbobenzoxy-L-proline phenylmethyl ester (124980-30-9)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 ℃; for 17h;

DOI:10.1016/S0040-4020(00)00771-7

upstream raw materials:

adamantyl isopropene

N-Benzyloxycarbonyl-L-proline

benzyl bromide

benzyl L-<(2-benzyloxycarbonyl)amino>-5-hydroxypentanoate

Downstream raw materials:

(S)-1-((S)-2-((benzyloxy)carbonyl)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-aminium chloride

(6S,9S,12S,14aS,20S,23S,25aS)-20-benzyl-6,12-di((S)-sec-butyl)-9-(hydroxymethyl)-23-isobutylhexadecahydro-1H-dipyrrolo[1,2-a:1',2'-j][1,4,7,10,13,16,19]heptaazacyclohenicosine-5,8,11,14,19,22,25(25aH)heptaone

benzyl (tert-butoxycarbonyl)-L-phenylalanyl-L-prolinate

Z-Pro-NH₂