(2R)-(-)-benzyl 2-(tert-butoxycarbonylamino)-3-(2-hydroxyethylsulfanyl)propanoate

Base Information

• Chemical Name: (2R)-(-)-benzyl 2-(tert-butoxycarbonylamino)-3-(2-hydroxyethylsulfanyl)propanoate
• CAS No.: 159380-94-6
• Molecular Formula: C₁₇H₂₅NO₅S
• Molecular Weight: 355.455
• Mol file: 159380-94-6.mol

Synonyms:(2R)-(-)-benzyl 2-(tert-butoxycarbonylamino)-3-(2-hydroxyethylsulfanyl)propanoate

Chemical Property of (2R)-(-)-benzyl 2-(tert-butoxycarbonylamino)-3-(2-hydroxyethylsulfanyl)propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-(-)-benzyl 2-(tert-butoxycarbonylamino)-3-(2-hydroxyethylsulfanyl)propanoate

There total 6 articles about (2R)-(-)-benzyl 2-(tert-butoxycarbonylamino)-3-(2-hydroxyethylsulfanyl)propanoate 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: 92.0%

Iodoethanol (624-76-0) + (R)-benzyl 2-((tert-butoxycarbonyl)amino)-3-mercaptopropanoate (92278-78-9) → (2R)-(-)-benzyl 2-(tert-butoxycarbonylamino)-3-(2-hydroxyethylsulfanyl)propanoate (159380-94-6)

Guidance literature:

With potassium carbonate; In acetone; at 20 ℃;

DOI:10.1016/j.bmc.2019.05.005

Reference yield:

di-t-butoxycarbonyl-L-cystine (10389-65-8) → (2R)-(-)-benzyl 2-(tert-butoxycarbonylamino)-3-(2-hydroxyethylsulfanyl)propanoate (159380-94-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 10 h / 20 °C

2.1: tributylphosphine / tetrahydrofuran / 0.5 h / 20 °C

2.2: 1 h / 20 °C

3.1: potassium carbonate / acetone / 20 °C

With tributylphosphine; potassium carbonate; In tetrahydrofuran; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.bmc.2019.05.005

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (2R)-(-)-benzyl 2-(tert-butoxycarbonylamino)-3-(2-hydroxyethylsulfanyl)propanoate (159380-94-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / water / 0 - 20 °C

2.1: potassium carbonate / N,N-dimethyl-formamide / 10 h / 20 °C

3.1: tributylphosphine / tetrahydrofuran / 0.5 h / 20 °C

3.2: 1 h / 20 °C

4.1: potassium carbonate / acetone / 20 °C

With tributylphosphine; potassium carbonate; triethylamine; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.bmc.2019.05.005

upstream raw materials:

benzyl bromide

(R)-2-tert-Butoxycarbonylamino-3-(2-hydroxy-ethylsulfanyl)-propionic acid

(-)-(2R)-2-amino-3-(2-hydroxyethylsulfanyl)propanoic acid

di-tert-butyl dicarbonate

Downstream raw materials:

(2R)-(+)-benzyl 3-(2-azidoethylsulfonyl)-2-(tert-butoxycarbonylamino)propanoate

(2R)-(-)-benzyl 3-(2-azidoethylsulfanyl)-2-(tert-butoxycarbonylamino)propanoate

(2R)-(-)-benzyl 2-(tert-butoxycarbonylamino)-3-(2-hydroxyethylsulfonyl)propanoate