(2R,3S)-2-Chloro-3-hydroxy-3-(1-trityl-1H-imidazol-4-yl)-propionamide

Base Information

• Chemical Name: (2R,3S)-2-Chloro-3-hydroxy-3-(1-trityl-1H-imidazol-4-yl)-propionamide
• CAS No.: 135793-04-3
• Molecular Formula: C₂₅H₂₂ClN₃O₂
• Molecular Weight: 431.922
• Mol file: 135793-04-3.mol

Synonyms:(2R,3S)-2-Chloro-3-hydroxy-3-(1-trityl-1H-imidazol-4-yl)-propionamide

Chemical Property of (2R,3S)-2-Chloro-3-hydroxy-3-(1-trityl-1H-imidazol-4-yl)-propionamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-2-Chloro-3-hydroxy-3-(1-trityl-1H-imidazol-4-yl)-propionamide

There total 2 articles about (2R,3S)-2-Chloro-3-hydroxy-3-(1-trityl-1H-imidazol-4-yl)-propionamide 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: 94.0%

(R)-3-[(2R,3S)-2-Chloro-3-hydroxy-3-(1-trityl-1H-imidazol-4-yl)-propionyl]-4-isopropyl-oxazolidin-2-one (135793-03-2) → (2R,3S)-2-Chloro-3-hydroxy-3-(1-trityl-1H-imidazol-4-yl)-propionamide (135793-04-3)

Guidance literature:

With ammonium hydroxide; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1016/S0040-4039(00)93492-0

Reference yield:

(1-tritylimidazol-4-yl)carboxaldehyde (33016-47-6) → (2R,3S)-2-Chloro-3-hydroxy-3-(1-trityl-1H-imidazol-4-yl)-propionamide (135793-04-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) Bu₂BOTf, NEt₃ / 1) CH₂Cl₂, -70 to 20 deg C, 2h, 2a) -75 deg C, 0.5h, 2b) 0 deg C, 2h

2: 94 percent / aq. NH₃ / tetrahydrofuran / 0.5 h / 20 °C

With ammonium hydroxide; di-n-butylboryl trifluoromethanesulfonate; triethylamine; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)93492-0

Reference yield: 86.0%

(2R,3S)-2-Chloro-3-hydroxy-3-(1-trityl-1H-imidazol-4-yl)-propionamide (135793-04-3) → (1S,2S)-3-Amino-2-chloro-1-(1-trityl-1H-imidazol-4-yl)-propan-1-ol (135910-46-2)

Guidance literature:

With dimethylsulfide borane complex; In tetrahydrofuran; for 0.5h; Heating;

DOI:10.1016/S0040-4039(00)93492-0

upstream raw materials:

(R)-3-[(2R,3S)-2-Chloro-3-hydroxy-3-(1-trityl-1H-imidazol-4-yl)-propionyl]-4-isopropyl-oxazolidin-2-one

(1-tritylimidazol-4-yl)carboxaldehyde

Downstream raw materials:

(1S,2S)-3-Amino-2-chloro-1-(1-trityl-1H-imidazol-4-yl)-propan-1-ol

{(2S,3S)-2-Chloro-3-[2-(4-chloro-phenylazo)-1H-imidazol-4-yl]-3-hydroxy-propyl}-carbamic acid tert-butyl ester

girolline

[(2S,3S)-2-Chloro-3-hydroxy-3-(1-trityl-1H-imidazol-4-yl)-propyl]-carbamic acid tert-butyl ester