tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)(methyl)amino)-2-hydroxybutanoate

Base Information

• Chemical Name: tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)(methyl)amino)-2-hydroxybutanoate
• CAS No.: 299926-08-2
• Molecular Formula: C₁₇H₂₅NO₅
• Molecular Weight: 323.389
• Mol file: 299926-08-2.mol

Synonyms:tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)(methyl)amino)-2-hydroxybutanoate

Chemical Property of tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)(methyl)amino)-2-hydroxybutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)(methyl)amino)-2-hydroxybutanoate

There total 5 articles about tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)(methyl)amino)-2-hydroxybutanoate 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: 89.0%

(2R,3S)-tert-Butyl 2-tert-butyldimethylsilyloxy-3-(N-benzyloxycarbonyl-N-methyl)aminobutanoate (299926-06-0) → tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)(methyl)amino)-2-hydroxybutanoate (299926-08-2)

Guidance literature:

With hydrogen fluoride; In acetonitrile; at 0 - 25 ℃; for 1.5h;

DOI:10.1055/s-2000-6417

Reference yield:

tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)amino)-2-hydroxybutanoate (203064-74-8) → tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)(methyl)amino)-2-hydroxybutanoate (299926-08-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 97 percent / imidazole / dimethylformamide / 20 h / 25 °C

2.1: NaH / tetrahydrofuran

2.2: 90 percent / tetrahydrofuran / 44 h

3.1: 89 percent / HF / acetonitrile / 1.5 h / 0 - 25 °C

With 1H-imidazole; hydrogen fluoride; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile; 1.1: Substitution / 2.1: Metallation / 2.2: Methylation / 3.1: Substitution;

DOI:10.1055/s-2000-6417

Reference yield:

tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)amino)-2-((tert-butyldimethylsilyl)oxy)butanoate (299926-04-8) → tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)(methyl)amino)-2-hydroxybutanoate (299926-08-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / tetrahydrofuran

1.2: 90 percent / tetrahydrofuran / 44 h

2.1: 89 percent / HF / acetonitrile / 1.5 h / 0 - 25 °C

With hydrogen fluoride; sodium hydride; In tetrahydrofuran; acetonitrile; 1.1: Metallation / 1.2: Methylation / 2.1: Substitution;

DOI:10.1055/s-2000-6417

upstream raw materials:

(2R,3S)-tert-Butyl 2-tert-butyldimethylsilyloxy-3-(N-benzyloxycarbonyl-N-methyl)aminobutanoate

tert-butyl (E)-crotonate

benzyl N-chlorocarbamate

tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)amino)-2-hydroxybutanoate

Downstream raw materials:

tert-butyl (2S,3S)-2-azido-3-(((benzyloxy)carbonyl)(methyl)amino)butanoate

(1R,2S)-2-(N-Benzyloxycarbonyl-N-methyl)amino-1-(tert-butoxycarbonyl)propyl-1-methanesulfonate