Didemnin B

Base Information

• Chemical Name: Didemnin B
• CAS No.: 77327-05-0
• Molecular Formula: C₅₇H₈₉N₇O₁₅
• Molecular Weight: 1112.37
• UNII: OR65D8FK1B
• DSSTox Substance ID: DTXSID80228068
• Wikidata: Q27137213
• NCI Thesaurus Code: C1364
• ChEMBL ID: CHEMBL414042
• Mol file: 77327-05-0.mol

Synonyms:didemnin A;didemnin A, N-(1-(2-hydroxy-1-oxopropyl)-L-prolyl)-, (S)-;didemnin A, N-(2-hydroxy-1-oxopropyl)-, (S)-;didemnin B;didemnin C;didemnin D;didemnin E;didemnins;NSC 325319;oncoprecipitin A

Chemical Property of Didemnin B

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6910 (estimate)
• Boiling Point: 1274.4°C at 760 mmHg
• Flash Point: 724.5°C
• PSA: 287.90000
• Density: 1.24g/cm³
• LogP: 3.17870
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 15
• Exact Mass: 1111.64166516
• Heavy Atom Count: 79
• Complexity: 2150

Purity/Quality:

99%, ^*data from raw suppliers

DIDEMNIN B 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C1C(CC(=O)OC(C(=O)C(C(=O)NC(C(=O)N2CCCC2C(=O)N(C(C(=O)OC(C(C(=O)N1)NC(=O)C(CC(C)C)N(C)C(=O)C3CCCN3C(=O)C(C)O)C)CC4=CC=C(C=C4)OC)C)CC(C)C)C)C(C)C)O
• Isomeric SMILES: CC[C@H](C)[C@@H]1[C@H](CC(=O)O[C@H](C(=O)[C@@H](C(=O)N[C@H](C(=O)N2CCC[C@H]2C(=O)N([C@H](C(=O)O[C@@H]([C@@H](C(=O)N1)NC(=O)[C@@H](CC(C)C)N(C)C(=O)[C@@H]3CCCN3C(=O)[C@H](C)O)C)CC4=CC=C(C=C4)OC)C)CC(C)C)C)C(C)C)O

Technology Process of Didemnin B

There total 84 articles about Didemnin B 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: 100.0%

Z-didemnin B (120286-08-0) → didemnin B (114607-50-0,128821-14-7,77327-05-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In isopropyl alcohol; at 20 ℃; for 2h; under 750.06 Torr;

DOI:10.1055/s-1991-26448

Reference yield: 49.0%

O-benzyldidemnin B (110720-14-4) → didemnin B (114607-50-0,128821-14-7,77327-05-0)

Guidance literature:

With formic acid; palladium; In methanol; for 6h;

DOI:10.1021/ja00184a041

Reference yield:

N-methyl-N-(benzyloxycarbonyl)-D-leucine (65635-85-0) → didemnin B (114607-50-0,128821-14-7,77327-05-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / triphenylphosphine / CH₂Cl₂ / 1 h / 20 °C

2: 99 percent / 2,4,6-collidine / CH₂Cl₂ / 2 h / 20 °C

3: 100 percent / hydrogen / 5 percent Pd-C / aq. acetic acid; aq. HCl / 5 h / 20 °C / 750.06 Torr

4: collidine / CH₂Cl₂ / 2 h

5: 100 percent / hydrogen / 5 percent Pd-C / propan-2-ol / 2 h / 20 °C / 750.06 Torr

With 2,4,6-trimethyl-pyridine; 2,3,5-trimethyl-pyridine; hydrogen; triphenylphosphine; palladium on activated charcoal; In hydrogenchloride; dichloromethane; acetic acid; isopropyl alcohol;

DOI:10.1055/s-1991-26448

upstream raw materials:

L-lactyl-L-prolyl-N-methyl-D-leucine

cyclo--5-methylheptanoyl>oxy-3-oxo-2,5-dimethylhexanoyl>-L-leucyl>-L-prolyl-N,O-dimethyl-L-tyrosyl>-L-threonyl> hydrochloride

Z-didemnin B

O-benzyldidemnin B

Refernces

• 1、 Schmidt,Kroner,Griesser. "Total synthesis of the didemnins; IV. Synthesis of the peptolide ring and construction of the side chain". . p. 294 - 300. Retrieved 2007/10/02.
• 2、 Hamada,Kondo,Shibata,Shioiri. "Efficient total synthesis of didemnins A and B". . p. 669 - 673. Retrieved 2007/10/02.