1,3-Propanediol, 2-azido-1-(4-nitrophenyl)-, (1R,2R)-

Base Information

• Chemical Name: 1,3-Propanediol, 2-azido-1-(4-nitrophenyl)-, (1R,2R)-
• CAS No.: 142917-86-0
• Molecular Formula: C9H10N4O4
• Molecular Weight: 238.203
• Mol file: 142917-86-0.mol

Synonyms:

Chemical Property of 1,3-Propanediol, 2-azido-1-(4-nitrophenyl)-, (1R,2R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,3-Propanediol, 2-azido-1-(4-nitrophenyl)-, (1R,2R)-

There total 9 articles about 1,3-Propanediol, 2-azido-1-(4-nitrophenyl)-, (1R,2R)- 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: 81.0%

(1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol (119-62-0,716-61-0,2792-51-0,2792-52-1,2964-48-9,3689-55-2,63526-31-8,71115-69-0,140694-64-0) → (1R,2R)-2-Azido-1-(4-nitro-phenyl)-propane-1,3-diol (142917-86-0)

Guidance literature:

With N-diazosulfamoyl fluoride; potassium hydrogencarbonate; In tert-butyl methyl ether; water; N,N-dimethyl-formamide; at 20 ℃; for 0.0833333h;

DOI:10.1038/s41586-019-1589-1

Reference yield:

[(2S,3R)-3-(4-Nitro-phenyl)-oxiranyl]-methanol (143058-48-4) → (1R,2R)-2-Azido-1-(4-nitro-phenyl)-propane-1,3-diol (142917-86-0)

Guidance literature:

With sodium azide; silica gel; In N,N-dimethyl-formamide; at 80 ℃;

DOI:10.1039/c39920000859

Reference yield:

p-nitrobenzene iodide (636-98-6) → (1R,2R)-2-Azido-1-(4-nitro-phenyl)-propane-1,3-diol (142917-86-0)

Guidance literature:

Multi-step reaction with 4 steps

1: Pd(PPh₃)4 / benzene

2: H₂ / Pd/CaCO₃

3: titanium isopropoxide (TIP), (+)-diethyl tartrate ((+)-DET), tert-butyl hydroperoxide (TBHP) / 168 h / -20 °C

4: NaN₃/silica gel / dimethylformamide / 80 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide; diethyl (2R,3R)-tartrate; hydrogen; silica gel; Lindlar's catalyst; In N,N-dimethyl-formamide; benzene;

DOI:10.1039/c39920000859

upstream raw materials:

[(2S,3R)-3-(4-Nitro-phenyl)-oxiranyl]-methanol

p-nitrobenzene iodide

3-(4-nitrophenyl)propyl-2-en-1-ol

3-(4-nitrophenyl)prop-2-yn-1-ol

Downstream raw materials:

chloramphenicol

(1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol

Refernces

• 1、 -. "TRIAZOLE COMPOUNDS AND METHODS OF MAKING AND USING THE SAME". Page/Page column 317. . Retrieved 2008/06/13.
• 2、 Rao,Rao,Bhanu. "Asymmetric synthesis of chloramphenicol". . p. 859 - 860. Retrieved 2007/10/02.