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

Base Information

• Chemical Name: tert-butyl (2S,3S)-2-azido-3-(((benzyloxy)carbonyl)(methyl)amino)butanoate
• CAS No.: 299926-12-8
• Molecular Formula: C₁₇H₂₄N₄O₄
• Molecular Weight: 348.402
• Mol file: 299926-12-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about tert-butyl (2S,3S)-2-azido-3-(((benzyloxy)carbonyl)(methyl)amino)butanoate 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: 57.0%

(1R,2S)-2-(N-Benzyloxycarbonyl-N-methyl)amino-1-(tert-butoxycarbonyl)propyl-1-methanesulfonate (299926-10-6) → tert-butyl (2S,3S)-2-azido-3-(((benzyloxy)carbonyl)(methyl)amino)butanoate (299926-12-8)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 75 ℃; for 19h;

DOI:10.1055/s-2000-6417

Reference yield:

(1R,2S)-2-(N-Benzyloxycarbonyl-N-methyl)amino-1-(tert-butoxycarbonyl)propyl-1-methanesulfonate (299926-10-6) → tert-butyl (2R,3S)-2-azido-3-(((benzyloxy)carbonyl)(methyl)amino)butanoate + tert-butyl (2S,3S)-2-azido-3-(((benzyloxy)carbonyl)(methyl)amino)butanoate (299926-12-8)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 80 ℃; for 21h; Overall yield = 116 mg;

DOI:10.1002/chem.202003387

Reference yield:

tert-butyl (E)-crotonate (79218-15-8) → tert-butyl (2S,3S)-2-azido-3-(((benzyloxy)carbonyl)(methyl)amino)butanoate (299926-12-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: (DHQ)2PHAL; aq. K₂OsO₂(OH)4 / acetonitrile

2.1: 97 percent / imidazole / dimethylformamide / 20 h / 25 °C

3.1: NaH / tetrahydrofuran

3.2: 90 percent / tetrahydrofuran / 44 h

4.1: 89 percent / HF / acetonitrile / 1.5 h / 0 - 25 °C

5.1: 91 percent / Et₃N / CH₂Cl₂ / 2.5 h / 25 °C

6.1: 57 percent / NaN₃ / dimethylformamide / 19 h / 75 °C

With 1H-imidazole; sodium azide; Hydroquinone 1,4-phthalazinediyl diether; potassium dioxotetrahydroxoosmate(VI); hydrogen fluoride; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Addition / 2.1: Substitution / 3.1: Metallation / 3.2: Methylation / 4.1: Substitution / 5.1: Substitution / 6.1: Substitution;

DOI:10.1055/s-2000-6417

upstream raw materials:

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

tert-butyl (E)-crotonate

benzyl N-chlorocarbamate

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