Bottromycin

Base Information

• Chemical Name: Bottromycin
• CAS No.: 15005-62-6
• Molecular Formula: C42H62 N8 O7 S
• Molecular Weight: 823.07
• Wikipedia: Bottromycin
• Wikidata: Q15634144
• Mol file: 15005-62-6.mol

Synonyms:bottromycin A(2);bottromycin A2

Chemical Property of Bottromycin

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1061.3°Cat760mmHg
• Flash Point: 595.7°C
• PSA: 242.49000
• Density: 1.28g/cm³
• LogP: 5.47390
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 15
• Exact Mass: 822.44621752
• Heavy Atom Count: 58
• Complexity: 1520

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCN2C1C(=O)NC(C(=O)NC(C(=NCC2=O)NC(C(=O)NC(C(C)C3=CC=CC=C3)C(=O)NC(CC(=O)OC)C4=NC=CS4)C(C)(C)C)C(C)(C)C)C(C)C

Technology Process of Bottromycin

There total 31 articles about Bottromycin 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: 51.0%

N-{[(3R)-3-methyl-L-prolinyl]-L-valinyl-[L-(carboxymethylimino)-tert-leucyl]-L-tert-leucyl-[(3S)-3-methyl-L-phenylalanyl]}-3-amino-3-(thiazol-2-yl)propanoic acid methyl ester hydrochloride (1138161-47-3) → bottromycin A2 (15005-62-6)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1002/anie.200804138

Reference yield: 8.0%

C35H54N6O6 → bottromycin A2 (15005-62-6)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; Reagent/catalyst; Solvent;

DOI:10.1021/acs.joc.8b00045

Reference yield: 7.0%

C35H54N6O6 → bottromycin A2 (15005-62-6) + C43H61N7O6S

Guidance literature:

With N-ethyl-N,N-diisopropylamine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In methanol; Reagent/catalyst; Solvent;

DOI:10.1021/acs.joc.8b00045

upstream raw materials:

N-{[(3R)-3-methyl-L-prolinyl]-L-valinyl-[L-(carboxymethylimino)-tert-leucyl]-L-tert-leucyl-[(3S)-3-methyl-L-phenylalanyl]}-3-amino-3-(thiazol-2-yl)propanoic acid methyl ester hydrochloride

(R)-3-[(2S,3S)-2-amino-3-phenylbutyrylamino]-3-(thiazol-2-yl)propanoic acid methyl ester

N-{N'-tert-butoxycarbonyl-L-tert-leucyl-[(3S)-3-methyl-L-phenylalanyl]}-3-amino-3-(thiazol-2-yl)propanoic acid methyl ester

N-{L-tert-leucyl-[(3S)-3-methyl-L-phenylalanyl]}-3-amino-3-(thiazol-2-yl)propanoic acid methyl ester

Downstream raw materials:

(R)-3-[(2S,3S)-2-amino-3-phenylbutyrylamino]-3-(thiazol-2-yl)propanoic acid methyl ester

C₂₅H₄₁N₅O₄

N-{[(3R)-3-methyl-L-prolinyl]-L-valinyl-[L-(2-hydroxyethyl)imino-tert-leucyl]-L-tert-leucyl-[(3S)-3-methyl-L-phenylalanyl]}-3-amino-3-(thiazol-2-yl)propanoic acid methyl ester

Refernces

• 1、 Shimamura, Hiroyuki,Gouda, Hiroaki,Nagai, Kenichiro,Hirose, Tomoyasu,Ichioka, Maki,Furuya, Yujiro,Kobayashi, Yutaka,Hirono, Shuichi,Sunazuka, Toshiaki,Omura, Satoshi. "Structure determination and total synthesis of bottromycin A2: A potent antibiotic against MRSA and VRE". supporting information; experimental part. p. 914 - 917. Retrieved 2009/05/15.