Cbz-Hyp(tBu)-D-Pro-OMe

Base Information

• Chemical Name: Cbz-Hyp(tBu)-D-Pro-OMe
• CAS No.: 545380-39-0
• Molecular Formula: C₂₃H₃₂N₂O₆
• Molecular Weight: 432.517
• DSSTox Substance ID: DTXSID801122041
• Nikkaji Number: J1.835.567A
• Mol file: 545380-39-0.mol

Synonyms:DTXSID801122041;545380-39-0;D-Proline, (4R)-4-(1,1-dimethylethoxy)-1-[(phenylmethoxy)carbonyl]-L-prolyl-, methyl ester

Chemical Property of Cbz-Hyp(tBu)-D-Pro-OMe

Chemical Property:

• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 432.22603674
• Heavy Atom Count: 31
• Complexity: 655

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC1CC(N(C1)C(=O)OCC2=CC=CC=C2)C(=O)N3CCCC3C(=O)OC
• Isomeric SMILES: CC(C)(C)O[C@@H]1C[C@H](N(C1)C(=O)OCC2=CC=CC=C2)C(=O)N3CCC[C@@H]3C(=O)OC

Technology Process of Cbz-Hyp(tBu)-D-Pro-OMe

There total 3 articles about Cbz-Hyp(tBu)-D-Pro-OMe 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:

Z-D-proline (6404-31-5) → methyl (2R)-1-([(2S,4R)-4-tert-butoxy-1-(benzyloxycarbonyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carboxylate (545380-39-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / DMAP; WSC*HCl / CHCl₃ / 1 h / 20 °C

2: H₂ / Pd(OH)2 / methanol / 19 h / 20 °C

3: 5.10 g / WSC*HCl; HOBt / CHCl₃ / 22 h / 20 °C

With dmap; WSC*HCl; hydrogen; benzotriazol-1-ol; palladium dihydroxide; In methanol; chloroform;

DOI:10.1021/jm051205r

Reference yield:

methyl (2R)-(benzyloxycarbonyl)pyrrolidine-2-carboxylate (182210-00-0) → methyl (2R)-1-([(2S,4R)-4-tert-butoxy-1-(benzyloxycarbonyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carboxylate (545380-39-0)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd(OH)2 / methanol / 19 h / 20 °C

2: 5.10 g / WSC*HCl; HOBt / CHCl₃ / 22 h / 20 °C

With WSC*HCl; hydrogen; benzotriazol-1-ol; palladium dihydroxide; In methanol; chloroform;

DOI:10.1021/jm051205r

Reference yield:

methyl (2R)-pyrrolidine-2-carboxylate (43041-12-9) + (2S,4R)-4-tert-butoxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (85201-91-8) → methyl (2R)-1-([(2S,4R)-4-tert-butoxy-1-(benzyloxycarbonyl)pyrrolidin-2-yl]carbonyl)pyrrolidine-2-carboxylate (545380-39-0)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In chloroform;

DOI:10.1016/S0960-894X(02)00843-0

upstream raw materials:

methyl (2R)-pyrrolidine-2-carboxylate

(2S,4R)-4-tert-butoxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

Z-D-proline

methyl (2R)-(benzyloxycarbonyl)pyrrolidine-2-carboxylate

Downstream raw materials:

(2R)-1-[((2S,4R)-4-tert-butoxy-1-[3,3,3-tris(4-fluorophenyl)propanoyl]pyrrolidin-2-yl)carbonyl]pyrrolidine-2-carboxylic acid

methyl (2R)-1-[((2S,4R)-4-tert-butoxy-1-[3,3,3-tris(4-fluorophenyl)propanoyl]pyrrolidin-2-yl)carbonyl]pyrrolidine-2-carboxylate

(2R)-1-{(2S,4R)-4-hydroxy-1-(3,3,3-triphenylpropanoyl)-pyrrolidin-2-yl}carbonyl-N-(4-piperidylmethyl)pyrrolidine-2-carboxamide

(2R)-1-{(2S,4R)-4-hydroxy-1-(3,3,3-triphenylpropanoyl)-pyrrolidin-2-yl}carbonyl-N-((3R)-3-piperidylmethyl)pyrrolidine-2-carboxamide