(2R,3R)-3-(benzyloxycarbonyl)amino-2-(t-butoxycarbonyl)amino-1-butanol

Base Information

• Chemical Name: (2R,3R)-3-(benzyloxycarbonyl)amino-2-(t-butoxycarbonyl)amino-1-butanol
• CAS No.: 156173-94-3
• Molecular Formula: C₁₇H₂₆N₂O₅
• Molecular Weight: 338.404
• Mol file: 156173-94-3.mol

Synonyms:(2R,3R)-3-(benzyloxycarbonyl)amino-2-(t-butoxycarbonyl)amino-1-butanol

Chemical Property of (2R,3R)-3-(benzyloxycarbonyl)amino-2-(t-butoxycarbonyl)amino-1-butanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-3-(benzyloxycarbonyl)amino-2-(t-butoxycarbonyl)amino-1-butanol

There total 10 articles about (2R,3R)-3-(benzyloxycarbonyl)amino-2-(t-butoxycarbonyl)amino-1-butanol 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: 90.0%

(R)-4-<(R)-1-(benzyloxycarbonylamino)ethyl>-3-t-butoxycarbonyl-2,2-dimethyl-1,3-oxazolidine (156173-93-2) → (2R,3R)-3-(benzyloxycarbonyl)amino-2-(t-butoxycarbonyl)amino-1-butanol (156173-94-3)

Guidance literature:

With acetic acid; for 16h; Ambient temperature;

DOI:10.1246/bcsj.68.1369

Reference yield:

(R)-3-t-butoxycarbonyl-2,2-dimethyl-4-<(S)-1-hydroxyethyl>-1,3-oxazolidine (156173-90-9) → (2R,3R)-3-(benzyloxycarbonyl)amino-2-(t-butoxycarbonyl)amino-1-butanol (156173-94-3)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / CH₂Cl₂ / 0.08 h / -10 °C

2: 85 percent / NaN₃, 15-crown-5, HMPA / 5 h / 70 °C

3: EtOH / 10percent Pd/C / 6 h / Ambient temperature

4: Et₃N / ethanol / 1 h / Ambient temperature

5: 90 percent / 70percent AcOH / 16 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium azide; 15-crown-5; ethanol; acetic acid; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane;

DOI:10.1246/bcsj.68.1369

Reference yield:

(4R)-4-[(R)-1-hydroxyethyl]-2,2-dimethyl-N-(tert-butoxycarbonyl)-1,3-oxazolidine (156173-83-0) → (2R,3R)-3-(benzyloxycarbonyl)amino-2-(t-butoxycarbonyl)amino-1-butanol (156173-94-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) Ph₃P, 2.) diethyl azodicarboxylate / 1.) THF, C₆H₆, 0 deg C, 8 min, 2.) THF, C₆H₆, a) 0 deg C, 10 min, b) RT, 5 h

2: 90 percent / K₂CO₃ / methanol / 12 h / Ambient temperature

3: Et₃N / CH₂Cl₂ / 0.08 h / -10 °C

4: 85 percent / NaN₃, 15-crown-5, HMPA / 5 h / 70 °C

5: EtOH / 10percent Pd/C / 6 h / Ambient temperature

6: Et₃N / ethanol / 1 h / Ambient temperature

7: 90 percent / 70percent AcOH / 16 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium azide; 15-crown-5; ethanol; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In methanol; ethanol; dichloromethane;

DOI:10.1246/bcsj.68.1369

upstream raw materials:

(R)-4-<(R)-1-(benzyloxycarbonylamino)ethyl>-3-t-butoxycarbonyl-2,2-dimethyl-1,3-oxazolidine

Boc-Thr-OH

N-Boc-O-benzyl-L-threonine

tert-butyl [(2R,3R)-3-(benzyloxy)-1-hydroxybutan-2-yl]carbamate