L-Proline, 1-[(2S)-2,6-bis[[(phenylmethoxy)carbonyl]amino]hexyl]-

Base Information

• Chemical Name: L-Proline, 1-[(2S)-2,6-bis[[(phenylmethoxy)carbonyl]amino]hexyl]-
• CAS No.: 184635-12-9
• Molecular Formula: C27H35N3O6
• Molecular Weight: 497.591
• DSSTox Substance ID: DTXSID10441288
• Wikidata: Q82258007
• Mol file: 184635-12-9.mol

Synonyms:184635-12-9;L-Proline, 1-[(2S)-2,6-bis[[(phenylmethoxy)carbonyl]amino]hexyl]-;DTXSID10441288

Chemical Property of L-Proline, 1-[(2S)-2,6-bis[[(phenylmethoxy)carbonyl]amino]hexyl]-

Chemical Property:

• XLogP3: 1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 15
• Exact Mass: 497.25258584
• Heavy Atom Count: 36
• Complexity: 678

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of L-Proline, 1-[(2S)-2,6-bis[[(phenylmethoxy)carbonyl]amino]hexyl]-

There total 4 articles about L-Proline, 1-[(2S)-2,6-bis[[(phenylmethoxy)carbonyl]amino]hexyl]- 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: 89.0%

Nα,Nε-bis(benzyloxycarbonyl)-D-lysinal (138207-66-6) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → (S)-1-((S)-2,6-Bis-benzyloxycarbonylamino-hexyl)-pyrrolidine-2-carboxylic acid (184635-12-9)

Guidance literature:

With sodium cyanoborohydride; In methanol; acetic acid; for 4h; Ambient temperature;

Reference yield:

N,N'-di-[(phenylmethoxy)carbonyl]-L-lysine (405-39-0) → (S)-1-((S)-2,6-Bis-benzyloxycarbonylamino-hexyl)-pyrrolidine-2-carboxylic acid (184635-12-9)

Guidance literature:

Multi-step reaction with 4 steps

2: TEA

3: LiAlH₄ / diethyl ether / 0 °C

4: 89 percent / NaBH₃CN / methanol; acetic acid / 4 h / Ambient temperature

With lithium aluminium tetrahydride; TEA; sodium cyanoborohydride; In methanol; diethyl ether; acetic acid;

Reference yield:

[(S)-5-Benzyloxycarbonylamino-5-(methoxy-methyl-carbamoyl)-pentyl]-carbamic acid benzyl ester → (S)-1-((S)-2,6-Bis-benzyloxycarbonylamino-hexyl)-pyrrolidine-2-carboxylic acid (184635-12-9)

Guidance literature:

Multi-step reaction with 2 steps

1: LiAlH₄ / diethyl ether / 0 °C

2: 89 percent / NaBH₃CN / methanol; acetic acid / 4 h / Ambient temperature

With lithium aluminium tetrahydride; sodium cyanoborohydride; In methanol; diethyl ether; acetic acid;

upstream raw materials:

N^α,N^ε-bis(benzyloxycarbonyl)-D-lysinal

L-proline

N,N'-di-[(phenylmethoxy)carbonyl]-L-lysine