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:

99% ^*data from raw suppliers

VIBRIOBACTIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: Vibriobactin is a catechol siderophore involved in iron acquisition, synthesized through a convergent total synthesis method featuring molybdenum(VI) oxide-catalyzed dehydrative cyclization as a key step. The process efficiently constructs the oxazoline moiety and employs selective protecting groups, such as the cyclic o-xylyl group, to achieve high reactivity and ease of removal, yielding vibriobactin in a 9-step sequence with a 50% overall yield.

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

Convergent total syntheses of fluvibactin and vibriobactin using molybdenum(vi) oxide-catalyzed dehydrative cyclization as a key step

10.1039/b805880f

In this study, an efficient and convergent total synthetic method is proposed for the synthesis of two catechol siderophores, fulvebactin and vibriomycin, in which a molybdenum(VI) oxide-catalyzed dehydration cyclization is the key step. The researchers used N-(o,m-dialkoxybenzoyl)-L-threonine derivatives to construct the 2-(o,m-dihydroxyphenyl)oxazoline moiety at an early stage. The molybdenum(VI) oxide-catalyzed method is effective for the synthesis of oxazolines, and this study explored various protecting groups on the catechol moiety and found that the cyclic o-xylyl group showed excellent reactivity and was easy to remove. The synthesis involved Sb(OEt)3-catalyzed ester-amide transformation to selectively synthesize diamides and monoamides, and WSCI?HCl and HOAt-promoted dehydration amide formation to achieve the final assembly. The o-xylyl group was removed by hydrogenolysis to obtain the target compounds, where the longest linear sequence required 9 steps starting from 2,3-dihydroxybenzoic acid, with an overall yield of 65% for fulvebactin and 50% for vibriomycin.