collismycin B

Base Information

• Chemical Name: collismycin B
• CAS No.: 158792-25-7
• Molecular Formula: C₁₃H₁₃N₃O₂S
• Molecular Weight: 275.331
• Mol file: 158792-25-7.mol

Synonyms:[2,2'-Bipyridine]-6-carboxaldehyde,4-methoxy-5-(methylthio)-, oxime, (Z)- (9CI); Collismycin B; SF 2738B

Chemical Property of collismycin B

Chemical Property:

• Vapor Pressure: 5.16E-06mmHg at 25°C
• Boiling Point: 381.2°Cat760mmHg
• Flash Point: 184.3°C
• PSA: 92.64000
• Density: 1.27g/cm³
• LogP: 2.59270

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of collismycin B

There total 17 articles about collismycin 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: 87.0%

4-methoxy-5-methylsulfanyl-[2,2′]bipyridinyl-6-carbaldehyde (205053-07-2) → collismycin A (158792-24-6,158792-25-7)

Guidance literature:

With hydroxylamine hydrochloride; sodium hydroxide; In ethanol; water; at 50 - 55 ℃; for 1h;

DOI:10.1021/op3003129

Reference yield:

2-Picolinic acid (98-98-6) → collismycin A (158792-24-6,158792-25-7)

Guidance literature:

With Streptomyces CLM-L mutant; at 30 ℃; for 144h;

DOI:10.1016/j.bmcl.2013.08.017

Reference yield:

2,2'-bipyridyl N-oxide (33421-43-1) → collismycin A (158792-24-6,158792-25-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 65 percent / KNO₃; H₂SO₄ / 2.5 h / 110 °C

2.1: 88 percent / methanol / 0.5 h / 40 °C

3.1: LDA / hexane; tetrahydrofuran / 1 h / -70 °C

3.2: 15 percent / BrCN / hexane; tetrahydrofuran / 0.25 h / -70 °C

4.1: 90 percent / PBr₃ / CHCl₃ / 0.75 h / Heating

5.1: LDA / tetrahydrofuran; hexane / 1 h / -70 °C

5.2: 61 percent / tetrahydrofuran; hexane / -70 - 20 °C

6.1: TMEDA; BuLi / diethyl ether; hexane / 0.5 h / -70 °C

6.2: 55 percent / diethyl ether; hexane / 0.75 h / -70 - -30 °C

7.1: 71 percent / hydroxylamine hydrochloride; pyridine / ethanol / 1 h / Heating

With pyridine; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; hydroxylamine hydrochloride; phosphorus tribromide; potassium nitrate; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; chloroform; 1.1: Nitration / 2.1: Substitution / 3.1: Metallation / 3.2: Bromination / 4.1: Reduction / 5.1: Metallation / 5.2: Oxidation / 6.1: Metallation / 6.2: Formylation / 7.1: Condensation;

DOI:10.1021/jo972022i

upstream raw materials:

collismycin A

4-methoxy-5-methylsulfanyl-[2,2′]bipyridinyl-6-carbaldehyde

[2,2]bipyridinyl

2,2'-bipyridyl N-oxide

Refernces

• 1、 Lopez-Ogalla, Javier,Saiz, Gonzalo,Palomo, Francisco E.. "Process development of a potent neuroprotector agent: Collismycin A". . p. 120 - 126. Retrieved 2013/03/29.
• 2、 Trécourt, Fran?ois,Gervais, Bruno,Mongin, Olivier,Gal, Catherine Le,Mongin, Florence,Quéguiner, Guy. "First Syntheses of Caerulomycin E and Collismycins A and C. A New Synthesis of Caerulomycin A". . p. 2892 - 2897. Retrieved 2007/10/03.