1-[(2R)-2-Hydroxy-4-methyl-1-oxopentyl]-L-proline phenylmethyl ester

Base Information

• Chemical Name: 1-[(2R)-2-Hydroxy-4-methyl-1-oxopentyl]-L-proline phenylmethyl ester
• CAS No.: 187753-73-7
• Molecular Formula: C₁₈H₂₅NO₄
• Molecular Weight: 319.401
• DSSTox Substance ID: DTXSID301160375
• Nikkaji Number: J1.346.104J
• Mol file: 187753-73-7.mol

Synonyms:DTXSID301160375;1-[(2R)-2-Hydroxy-4-methyl-1-oxopentyl]-L-proline phenylmethyl ester;187753-73-7

Chemical Property of 1-[(2R)-2-Hydroxy-4-methyl-1-oxopentyl]-L-proline phenylmethyl ester

Chemical Property:

• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 319.17835828
• Heavy Atom Count: 23
• Complexity: 404

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)CC(C(=O)N1CCCC1C(=O)OCC2=CC=CC=C2)O
• Isomeric SMILES: CC(C)C[C@H](C(=O)N1CCC[C@H]1C(=O)OCC2=CC=CC=C2)O

Technology Process of 1-[(2R)-2-Hydroxy-4-methyl-1-oxopentyl]-L-proline phenylmethyl ester

There total 1 articles about 1-[(2R)-2-Hydroxy-4-methyl-1-oxopentyl]-L-proline phenylmethyl 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: 95.0%

(R)-2-hydroxy-4-methylpentanoic acid (20312-37-2,498-36-2) + H-Pro-OBzl (41324-66-7) → (S)-1-((R)-2-Hydroxy-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid benzyl ester (187753-73-7)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide;

DOI:10.1016/S0040-4039(96)02346-5

Reference yield: 98.0%

3-(tert-butyloxycarbonylamino)propionic acid (3303-84-2) + (S)-1-((R)-2-Hydroxy-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid benzyl ester (187753-73-7) → (S)-1-[(R)-2-(3-tert-Butoxycarbonylamino-propionyloxy)-4-methyl-pentanoyl]-pyrrolidine-2-carboxylic acid benzyl ester (55739-22-5)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃; for 21h;

DOI:10.1021/jo015953+

Reference yield:

(S)-1-((R)-2-Hydroxy-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid benzyl ester (187753-73-7) → destruxin B (2503-26-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 98 percent / DCC; DMAP / CH₂Cl₂ / 21 h / 0 - 20 °C

2.1: H₂ / Pd/C / methanol / 2 h

3.1: 233 mg / DCC; HOBt hydrate / CH₂Cl₂ / 25 h / 0 - 20 °C

4.1: TFA / CH₂Cl₂ / 0.5 h / 20 °C

4.2: NaNO₂; aq. HCl / 0.25 h

4.3: 65 percent / aq. NaHCO₃ / CH₂Cl₂ / 15 h / 20 °C

With dmap; hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/jo015953+

upstream raw materials:

(R)-2-hydroxy-4-methylpentanoic acid

H-Pro-OBzl

Downstream raw materials:

(S)-1-[(R)-2-(3-tert-Butoxycarbonylamino-propionyloxy)-4-methyl-pentanoyl]-pyrrolidine-2-carboxylic acid benzyl ester

destruxin B

homodestruxin B

Refernces

• 1、 Ward, Dale E.,Lazny, Ryszard,Soledade,Pedras. "Synthesis of the host-selective phytotoxin destruxin B. Avoiding diketopiperazine formation from an N-methyl amino acid dipeptide by use of the Boc-hydrazide derivative". . p. 339 - 342. Retrieved 2007/10/03.