CID 16220095

Base Information

• Chemical Name: CID 16220095
• CAS No.: 21411-53-0
• Molecular Formula: C28H35 N3 O7
• Molecular Weight: 525.602
• Hs Code.: 29419090
• European Community (EC) Number: 244-376-6
• Metabolomics Workbench ID: 70640
• Nikkaji Number: J136.083C
• Wikipedia: Pristinamycin_IIA
• Mol file: 21411-53-0.mol

Synonyms:Ostreogrycin G;Pristinamycin IIA;Pristinamycin IIB;Staphylomycin M;Staphylomycin M1;Streptogramin A;Virginiamycin Factor M1;Virginiamycin IIB;Virginiamycin M1

Chemical Property of CID 16220095

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 165-167℃
• Boiling Point: 825.2 °C at 760 mmHg
• PKA: 13.18±0.70(Predicted)
• Flash Point: 452.9 °C
• PSA: 139.04000
• Density: 1.26 g/cm³
• LogP: 2.92610
• Storage Temp.: 2-8°C
• Solubility.: chloroform/methanol: soluble10mg/mL
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 1
• Exact Mass: 525.24750046
• Heavy Atom Count: 38
• Complexity: 1030

Purity/Quality:

99% ^*data from raw suppliers

Ostreogrycin A ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C=CC(=O)NCC=CC(=CC(CC(=O)CC2=NC(=CO2)C(=O)N3CCC=C3C(=O)OC1C(C)C)O)C
• Isomeric SMILES: C[C@@H]1/C=C\C(=O)NC/C=C\C(=C/[C@H](CC(=O)CC2=NC(=CO2)C(=O)N3CCC=C3C(=O)O[C@@H]1C(C)C)O)\C
• Uses: Ostreogrycin A (virginiamycin M1, streptogramin A) is the major component of the virginamycin complex. In the 1950s this complex was independently discovered so many times that the literature became highly confusing. Ostreogrycin A is a macrocyclic lactone antibiotic that acts synergistically with the structurally unrelated cyclic depsipeptides, virginiamycin B (ostreogrycin B, streptogramin B) and virginiamycin S, to inhibit peptide elongation. This is achieved by blocking formation of a peptide bond between the growing peptide chain (peptidyl-tRNA) linked to the 50S ribosome and aminoacyl-tRNA. Ostreogrycin A is highly active against Gram positive bacteria, particularly MRSA. Ostreogrycin A (virginiamycin M1, streptogramin A) is the major component of the virginiamycin complex. In the 1950s this complex was independently discovered so many times that the literature became highly confusing. Ostreogrycin A is a macrocyclic lactone antibiotic that acts synergistically with the structurally unrelated cyclic depsipeptides, virginiamycin B (ostreogrycin B, streptogramin B) and virginiamycin S, to inhibit peptide elongation. This is achieved by blocking formation of a peptide bond between the growing peptide chain (peptidyl-tRNA) linked to the 50S ribosome and aminoacyl-tRNA. Ostreogrycin A is highly active against Gram positive bacteria, particularly MRSA. Macrolactone antibiotic. Antibacterial; growth promotant.

Technology Process of CID 16220095

There total 16 articles about CID 16220095 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: 85.0%

C37H57N3O7Si2 → virginiamycin M1 (21411-53-0)

Guidance literature:

With 1H-imidazole hydrochloride; tetrabutyl ammonium fluoride; In tetrahydrofuran; for 12h;

Reference yield:

dalfopristin → virginiamycin M1 (21411-53-0)

Guidance literature:

With water; In aq. phosphate buffer; dimethyl sulfoxide; at 37 ℃; for 24h; pH=7.4; pH-value;

DOI:10.1128/AAC.03389-14

Reference yield:

C18H32BrNO2S2Si → virginiamycin M1 (21411-53-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: hexane; tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere; Sealed tube

1.2: 1 h / -78 °C / Inert atmosphere; Sealed tube

2.1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 2.08 h / 23 °C / Inert atmosphere; Sealed tube

3.1: 2,6-dimethylpyridine / dichloromethane / 23 °C / Inert atmosphere; Sealed tube

4.1: tris-(dibenzylideneacetone)dipalladium(0); bis(3,5-bis(trifluoromethyl)phenyl)(2’,4’,6’-triisopropyl-3,6-dimethoxy-[1,1’-biphenyl]-2-yl)phosphine / toluene / 24.5 h / 80 °C / Inert atmosphere; Sealed tube

5.1: Imidazole hydrochloride; tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 23 °C / Inert atmosphere; Sealed tube

With 2,6-dimethylpyridine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; bis(3,5-bis(trifluoromethyl)phenyl)(2’,4’,6’-triisopropyl-3,6-dimethoxy-[1,1’-biphenyl]-2-yl)phosphine; tetrabutyl ammonium fluoride; Imidazole hydrochloride; In tetrahydrofuran; hexane; dichloromethane; toluene; 4.1: |Stille Cross Coupling;

DOI:10.1021/jacs.7b08577

upstream raw materials:

methyl (4R,5R,E)-5-hydroxy-4,6-dimethylhept-2-enoate

(4R,5R,E)-5-hydroxy-4,6-dimethyl-N-(prop-2-yn- 1-yl)hept-2-enamide

Refernces

• 1、 -. "METHODS OF MAKING STREPTOGRAMIN COMPOSITIONS AND THE USE THEREOF". Paragraph 0777. . Retrieved 2019/02/15.