(2S,3R)-N-tert-butoxycarbonyl-N-methoxymethyl-α,β-dimethylphenylalanine ethyl ester

Base Information

• Chemical Name: (2S,3R)-N-tert-butoxycarbonyl-N-methoxymethyl-α,β-dimethylphenylalanine ethyl ester
• CAS No.: 860618-81-1
• Molecular Formula: C₂₀H₃₁NO₅
• Molecular Weight: 365.47
• Mol file: 860618-81-1.mol

Synonyms:

Chemical Property of (2S,3R)-N-tert-butoxycarbonyl-N-methoxymethyl-α,β-dimethylphenylalanine ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-N-tert-butoxycarbonyl-N-methoxymethyl-α,β-dimethylphenylalanine ethyl ester

There total 3 articles about (2S,3R)-N-tert-butoxycarbonyl-N-methoxymethyl-α,β-dimethylphenylalanine ethyl ester 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:

(2S,3R)-N-tert-butoxycarbonyl-N-methoxymethyl-β-methylphenylalanine ethyl ester + methyl iodide (74-88-4) → (2S,3R)-N-tert-butoxycarbonyl-N-methoxymethyl-α,β-dimethylphenylalanine ethyl ester (860618-81-1)

Guidance literature:

(2S,3R)-N-tert-butoxycarbonyl-N-methoxymethyl-β-methylphenylalanine ethyl ester; With potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 1h;

methyl iodide; In tetrahydrofuran; at -78 ℃; for 20h;

DOI:10.1055/s-2005-865337

Reference yield:

(2R,3R)-N-tert-butoxycarbonyl-N-methoxymethyl-β-methylphenylalanine ethyl ester + methyl iodide (74-88-4) → (2S,3R)-N-tert-butoxycarbonyl-N-methoxymethyl-α,β-dimethylphenylalanine ethyl ester (860618-81-1) + (2R,3R)-N-tert-butoxycarbonyl-N-methoxymethyl-α,β-dimethylphenylalanine ethyl ester

Guidance literature:

(2R,3R)-N-tert-butoxycarbonyl-N-methoxymethyl-β-methylphenylalanine ethyl ester; With potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 1h;

methyl iodide; In tetrahydrofuran; at -78 ℃; for 20h; Title compound not separated from byproducts;

DOI:10.1055/s-2005-865337

Reference yield:

(2S,3R)-N-tert-butoxycarbonyl-β-methylphenylalanine ethyl ester → (2S,3R)-N-tert-butoxycarbonyl-N-methoxymethyl-α,β-dimethylphenylalanine ethyl ester (860618-81-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: KHMDS / tetrahydrofuran / 0.5 h / -78 °C

1.2: 72 percent / tetrahydrofuran / 20 h / -78 - 20 °C

2.1: KHMDS / tetrahydrofuran / 1 h / -78 °C

2.2: tetrahydrofuran / 20 h / -78 °C

With potassium hexamethylsilazane; In tetrahydrofuran;

DOI:10.1055/s-2005-865337

upstream raw materials:

methyl iodide