Dextramycin

Base Information

• Chemical Name: Dextramycin
• CAS No.: 134-90-7
• Deprecated CAS: 13171-08-9,137731-89-6
• Molecular Formula: C11H12 Cl2 N2 O5
• Molecular Weight: 323.133
• Hs Code.: 2924299090
• European Community (EC) Number: 205-161-2
• UNII: U0PWV2Z3IW
• DSSTox Substance ID: DTXSID40158453
• Nikkaji Number: J184.390G
• Wikidata: Q27290527
• ChEMBL ID: CHEMBL1437336
• Mol file: 134-90-7.mol

Synonyms:dextramycine

Chemical Property of Dextramycin

Chemical Property:

• Vapor Pressure: 1.63E-17mmHg at 25°C
• Melting Point: 150-151 °C
• Refractive Index: 1.6300 (estimate)
• Boiling Point: 644.9°C at 760 mmHg
• PKA: 11.03±0.46(Predicted)
• Flash Point: 343.8°C
• PSA: 115.38000
• Density: 1.547g/cm³
• LogP: 1.82310
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Ethanol (Sparingly, Sonicated), Methanol (Slightly)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 322.0123269
• Heavy Atom Count: 20
• Complexity: 342

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(C(CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
• Isomeric SMILES: C1=CC(=CC=C1[C@@H]([C@H](CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
• Uses: The S,S-stereoisomer of Chloramphenicol (C325030). Broad spectrum antibiotic obtained from cultures of the soil bacterium Streptomyces venezuelae. It has a broad spectrum of activity against Gram-positive and gram-negative bacteria. Antibacterial; antirickettsial.

Technology Process of Dextramycin

There total 91 articles about Dextramycin 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: 79.0%

(2RS,3SR)-2-(2,2-dichloro-acetylamino)-3-hydroxy-3-(4-nitro-phenyl)-propionic acid ethyl ester (100381-03-1) → chlorampenicol (56-75-7,134-90-7,579-51-1,2787-09-9,3419-87-2,7384-89-6,7387-98-6,50762-99-7,126787-77-7,140694-65-1,85666-84-8)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.5h;

DOI:10.1021/ol901784m

Reference yield:

chloramphenicol (26367-75-9) → chlorampenicol (56-75-7,134-90-7,579-51-1,2787-09-9,3419-87-2,7384-89-6,7387-98-6,50762-99-7,126787-77-7,140694-65-1,85666-84-8)

Guidance literature:

With aluminum isopropoxide; isopropyl alcohol;

DOI:10.1021/ja01145a523

Reference yield:

(+/-)-threo-2-amino-1-phenyl-1,3-propanediol (3306-06-7,5285-86-9,28143-91-1,36391-67-0,36391-68-1,46032-98-8,55057-81-3,105452-39-9,119364-52-2) → chlorampenicol (56-75-7,134-90-7,579-51-1,2787-09-9,3419-87-2,7384-89-6,7387-98-6,50762-99-7,126787-77-7,140694-65-1,85666-84-8)

Guidance literature:

Multi-step reaction with 5 steps

2: pyridine

3: amidosulfuric acid; nitric acid

4: aqueous hydrochloric acid

With pyridine; hydrogenchloride; aminosulfonic acid; nitric acid;

DOI:10.1021/ja01175a066

upstream raw materials:

dichloroacetic acid methyl ester

(1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol

methanol

(1S)-10-camphorsulfonic acid

Downstream raw materials:

chloramphenicol

L-threo-chloramphenicol

(S)-2-(2,2-dichloro-acetylamino)-3-hydroxy-1-(4-nitro-phenyl)-propan-1-one

chloramphenicol

Refernces

• 1、 Jun,Jun,Shaorong,Hua,Quanyuan,Hansheng,Xianming. "Diastereoselective synthesis of (2R,4S,5S)-(+)-5-(2,2-Dichloroacetamido)- 4-(4-nitrophenyl)-2-aryl-1,3-dioxanes". . p. 515 - 518. Retrieved 2001.
• 2、 Prasad,Reddi,Sudalai. "Oxidant controlled regio- and stereodivergent azidohydroxylation of alkenes via I2 catalysis". supporting information. p. 10276 - 10279. Retrieved 2015/06/25.