tert-butyl (1R,2R)-2-methoxycarbonyl-2-{[(methylthio)carbonylthioxyl]oxy}-1-phenylethylcarbamate

Base Information

• Chemical Name: tert-butyl (1R,2R)-2-methoxycarbonyl-2-{[(methylthio)carbonylthioxyl]oxy}-1-phenylethylcarbamate
• CAS No.: 959123-36-5
• Molecular Formula: C₁₇H₂₃NO₅S₂
• Molecular Weight: 385.505
• Mol file: 959123-36-5.mol

Synonyms:tert-butyl (1R,2R)-2-methoxycarbonyl-2-{[(methylthio)carbonylthioxyl]oxy}-1-phenylethylcarbamate

Chemical Property of tert-butyl (1R,2R)-2-methoxycarbonyl-2-{[(methylthio)carbonylthioxyl]oxy}-1-phenylethylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (1R,2R)-2-methoxycarbonyl-2-{[(methylthio)carbonylthioxyl]oxy}-1-phenylethylcarbamate

There total 5 articles about tert-butyl (1R,2R)-2-methoxycarbonyl-2-{[(methylthio)carbonylthioxyl]oxy}-1-phenylethylcarbamate 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: 82.0%

carbon disulfide (75-15-0,12122-00-8) + tert-butyl (1R,2R)-2-methoxycarbonyl-2-hydroxy-1-phenylethylcarbamate (959123-35-4) + methyl iodide (74-88-4) → tert-butyl (1R,2R)-2-methoxycarbonyl-2-{[(methylthio)carbonylthioxyl]oxy}-1-phenylethylcarbamate (959123-36-5)

Guidance literature:

carbon disulfide; tert-butyl (1R,2R)-2-methoxycarbonyl-2-hydroxy-1-phenylethylcarbamate; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.5h;

methyl iodide; In tetrahydrofuran; at 0 ℃; for 2h; Further stages.;

DOI:10.1016/j.tetasy.2007.07.028

Reference yield:

methyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate (122743-18-4) → tert-butyl (1R,2R)-2-methoxycarbonyl-2-{[(methylthio)carbonylthioxyl]oxy}-1-phenylethylcarbamate (959123-36-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 90 percent / thionyl chloride; triethylamine / CH₂Cl₂ / 0.75 h / 0 °C

2.1: 80 percent / sodium azide / dimethylformamide / 48 h / 80 °C

3.1: 88 percent / Et₃N; hydrogen / Pd/C / ethyl acetate / 12 h / 20 °C / 760.05 Torr

4.1: sodium hydride / tetrahydrofuran; various solvent(s) / 0.5 h / 0 °C

4.2: 82 percent / tetrahydrofuran; various solvent(s) / 2 h / 0 °C

With thionyl chloride; sodium azide; hydrogen; sodium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/j.tetasy.2007.07.028

Reference yield:

Methyl (2R,3R)-(-)-2-hydroxy-3-azido-3-phenyl-propionate (127053-44-5) → tert-butyl (1R,2R)-2-methoxycarbonyl-2-{[(methylthio)carbonylthioxyl]oxy}-1-phenylethylcarbamate (959123-36-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 88 percent / Et₃N; hydrogen / Pd/C / ethyl acetate / 12 h / 20 °C / 760.05 Torr

2.1: sodium hydride / tetrahydrofuran; various solvent(s) / 0.5 h / 0 °C

2.2: 82 percent / tetrahydrofuran; various solvent(s) / 2 h / 0 °C

With hydrogen; sodium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate;

DOI:10.1016/j.tetasy.2007.07.028

upstream raw materials:

carbon disulfide

tert-butyl (1R,2R)-2-methoxycarbonyl-2-hydroxy-1-phenylethylcarbamate

methyl iodide

methyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate

Downstream raw materials:

methyl (3S)-3-[(tert-butoxycarbonyl)amino]-3-phenylpropionate

(S)-3-amino-3-phenylpropanol

S-(3-hydroxy-1-phenyl-propyl)-carbamic acid tert-butyl ester

Refernces