tert-butyl (1S,2R)-3-bromo-1-hydroxy-1-(4-nitrophenyl)propan-2-ylcarbamate

Base Information

• Chemical Name: tert-butyl (1S,2R)-3-bromo-1-hydroxy-1-(4-nitrophenyl)propan-2-ylcarbamate
• CAS No.: 1186120-57-9
• Molecular Formula: C₁₄H₁₉BrN₂O₅
• Molecular Weight: 375.219
• Mol file: 1186120-57-9.mol

Synonyms:tert-butyl (1S,2R)-3-bromo-1-hydroxy-1-(4-nitrophenyl)propan-2-ylcarbamate

Chemical Property of tert-butyl (1S,2R)-3-bromo-1-hydroxy-1-(4-nitrophenyl)propan-2-ylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (1S,2R)-3-bromo-1-hydroxy-1-(4-nitrophenyl)propan-2-ylcarbamate

There total 2 articles about tert-butyl (1S,2R)-3-bromo-1-hydroxy-1-(4-nitrophenyl)propan-2-ylcarbamate 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: 50.0%

(1S,2S)-(+)-2-tert-butoxycarbonylamino-1-(4-nitrophenyl)-1,3-propanediol (647376-90-7) → tert-butyl (1S,2R)-3-bromo-1-hydroxy-1-(4-nitrophenyl)propan-2-ylcarbamate (1186120-57-9)

Guidance literature:

With N-Bromosuccinimide; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; for 9.5h; regioselective reaction;

DOI:10.1016/j.bmc.2011.07.008

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → tert-butyl (1S,2R)-3-bromo-1-hydroxy-1-(4-nitrophenyl)propan-2-ylcarbamate (1186120-57-9)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 24 h / 20 °C

2: N-Bromosuccinimide; triphenylphosphine / tetrahydrofuran / 9.5 h / 0 - 20 °C

With N-Bromosuccinimide; triphenylphosphine; In tetrahydrofuran;

DOI:10.1016/j.bmc.2011.07.008

Reference yield: 87.0%

tert-butyl (1S,2R)-3-bromo-1-hydroxy-1-(4-nitrophenyl)propan-2-ylcarbamate (1186120-57-9) → tert-butyl(1S,2S)-3-azido-1-hydroxy-1-(4-nitrophenyl)propan-2-ylcarbamate (1186120-58-0)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 65 ℃; for 12h; Inert atmosphere;

DOI:10.1016/j.bmc.2011.07.008

upstream raw materials:

di-tert-butyl dicarbonate

(1S,2S)-(+)-2-tert-butoxycarbonylamino-1-(4-nitrophenyl)-1,3-propanediol

Downstream raw materials:

C₂₅H₄₀N₄O₈

C₂₅H₄₂N₄O₆

C₂₅H₄₀IN₃O₆

(S)-2-amino-N-((2S,3S)-2-amino-3-hydroxy-3-(4-nitrophenyl)propyl)-4-methylpentanamide hydrochloride