Pradimicin A

Base Information

• Chemical Name: Pradimicin A
• CAS No.: 117704-65-1
• Molecular Formula: C40H44 N2 O18
• Molecular Weight: 840.792
• DSSTox Substance ID: DTXSID201043968
• Nikkaji Number: J361.639H
• Wikidata: Q27108053
• ChEMBL ID: CHEMBL1673205
• Mol file: 117704-65-1.mol

Synonyms:BMY 28567;BMY-28567;pradimicin A

Chemical Property of Pradimicin A

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1120.3°Cat760mmHg
• Flash Point: 631.3°C
• PSA: 320.56000
• Density: 1.68g/cm³
• LogP: 0.17010
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 11
• Hydrogen Bond Acceptor Count: 19
• Rotatable Bond Count: 9
• Exact Mass: 840.25891256
• Heavy Atom Count: 60
• Complexity: 1610

Purity/Quality:

99% ^*data from raw suppliers

PRADIMICIN A 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC2C(C3=CC4=C(C(=C3C5=C2C=C(C(=C5O)C(=O)NC(C)C(=O)O)C)O)C(=O)C6=C(C4=O)C(=CC(=C6)OC)O)O)O)OC7C(C(C(CO7)O)O)O)NC
• Isomeric SMILES: C[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](C3=CC4=C(C(=C3C5=C2C=C(C(=C5O)C(=O)N[C@H](C)C(=O)O)C)O)C(=O)C6=C(C4=O)C(=CC(=C6)OC)O)O)O)O[C@H]7[C@@H]([C@H]([C@@H](CO7)O)O)O)NC

Technology Process of Pradimicin A

There total 2 articles about Pradimicin A 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:

4'-N-Cbz-pradimicin A methyl ester → pradimicin A -5,6,8,13-tetrahydro-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxobenzo<α>naphthacen-2-yl>carbonyl>-D-alanine> (117704-65-1)

Guidance literature:

With sodium hydroxide; hydrogen; Yield given. Multistep reaction;

DOI:10.1248/cpb.41.223

Reference yield:

C51H48N4O19 → pradimicin A -5,6,8,13-tetrahydro-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxobenzo<α>naphthacen-2-yl>carbonyl>-D-alanine> (117704-65-1)

Guidance literature:

Multi-step reaction with 2 steps

2: 1.) aq. NaOH, 2.) H₂

With sodium hydroxide; hydrogen;

DOI:10.1248/cpb.41.223

Reference yield: 79.0%

pradimicin A -5,6,8,13-tetrahydro-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxobenzo<α>naphthacen-2-yl>carbonyl>-D-alanine> (117704-65-1) → 4-nitro-pradimicin (153619-30-8)

Guidance literature:

With nitrosonium tetrafluoroborate; In acetonitrile; for 0.0833333h; Ambient temperature;

DOI:10.7164/antibiotics.46.1447

Downstream raw materials:

methyl xyloside

(R)-2-{[(5S,6S)-5-((2S,3R,4S,5R,6R)-3,4-Dihydroxy-6-methyl-5-methylamino-tetrahydro-pyran-2-yloxy)-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5,6,8,13-tetrahydro-benzo[a]naphthacene-2-carbonyl]-amino}-propionic acid methyl ester

D-Alanine

(5S,6S)-1,5,6,9,14-Pentahydroxy-11-methoxy-3-methyl-8,13-dioxo-5,6,8,13-tetrahydro-benzo[a]naphthacene-2-carboxylic acid

Refernces