vibriobactin

Base Information

• Chemical Name: vibriobactin
• CAS No.: 88217-23-6
• Molecular Formula: C35H39 N5 O11
• Molecular Weight: 705.722
• Mol file: 88217-23-6.mol

Synonyms:4-Oxazolecarboxamide,N-[3-[(2,3-dihydroxybenzoyl)amino]propyl]-2-(2,3-dihydroxyphenyl)-N-[3-[[[2-(2,3-dihydroxyphenyl)-4,5-dihydro-5-methyl-4-oxazolyl]carbonyl]amino]propyl]-4,5-dihydro-5-methyl-,[4S-[4a(4R*,5S*),5b]]-; Vibriobactin

Chemical Property of vibriobactin

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1056.9°C at 760 mmHg
• Flash Point: 593°C
• PSA: 243.07000
• Density: 1.457g/cm³
• LogP: 1.49620

Purity/Quality:

98% ^*data from raw suppliers

VIBRIOBACTIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of vibriobactin

There total 11 articles about vibriobactin 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: 99.0%

C59H57N5O11 (1058728-56-5) → N-[3-(2,3-dihydroxybenzamido)propyl]-1,3-bis[2-(2,3-dihydroxyphenyl)-trans-5-methyl-2-oxazoline-4-carboxamido]propane (88217-23-6)

Guidance literature:

With 10% Pd on charcoal; hydrogen; In ethanol; at 60 ℃; for 2h;

DOI:10.1039/b805880f

Reference yield: 58.0%

ethyl 2,3-dihydroxybenzimidate (96649-28-4) + N1,N4-bis[(L)-threonyl]-N7-(2,3-dimethoxybenzoyl)norspermidine dihydrobromide (96857-12-4) → N-[3-(2,3-dihydroxybenzamido)propyl]-1,3-bis[2-(2,3-dihydroxyphenyl)-trans-5-methyl-2-oxazoline-4-carboxamido]propane (88217-23-6)

Guidance literature:

In methanol; for 33h; Heating;

DOI:10.1016/S0040-4020(01)96492-0

Reference yield:

N1-(tert-butoxycarbonyl)-N8-(2,3-dimethoxybenzoyl)norspermidine (943136-36-5) → N-[3-(2,3-dihydroxybenzamido)propyl]-1,3-bis[2-(2,3-dihydroxyphenyl)-trans-5-methyl-2-oxazoline-4-carboxamido]propane (88217-23-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / trifluoroacetic acid / CH₂Cl₂ / 2 h / 0 - 20 °C

2: 90 percent / BBr₃ / CH₂Cl₂ / 20 h / 20 °C

With boron tribromide; trifluoroacetic acid; In dichloromethane;

DOI:10.1055/s-2007-965960

upstream raw materials:

ethyl 2,3-dihydroxybenzimidate

N¹,N⁴-bis[(L)-threonyl]-N⁷-(2,3-dimethoxybenzoyl)norspermidine dihydrobromide

N¹-(tert-butoxycarbonyl)-N⁸-(2,3-dimethoxybenzoyl)norspermidine

2,3-dimethoxybenzoic acid

Refernces

• 1、 Bergeron, Raymond J.,Bharti, Neelam,Singh, Shailendra. "Total synthesis of vulnibactin: A natural product iron chelator". . p. 1033 - 1037. Retrieved 2008/02/03.