(R)-4-benzyloxycarbonylamino-3-tert-butoxycarbonyl-2-oxazolidone

Base Information

• Chemical Name: (R)-4-benzyloxycarbonylamino-3-tert-butoxycarbonyl-2-oxazolidone
• CAS No.: 306773-79-5
• Molecular Formula: C₁₆H₂₀N₂O₆
• Molecular Weight: 336.345
• Mol file: 306773-79-5.mol

Synonyms:(R)-4-benzyloxycarbonylamino-3-tert-butoxycarbonyl-2-oxazolidone

Chemical Property of (R)-4-benzyloxycarbonylamino-3-tert-butoxycarbonyl-2-oxazolidone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-benzyloxycarbonylamino-3-tert-butoxycarbonyl-2-oxazolidone

There total 1 articles about (R)-4-benzyloxycarbonylamino-3-tert-butoxycarbonyl-2-oxazolidone 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: 95.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-4-benzyloxycarbonylamino-2-oxazolidone (7705-88-6) → (R)-4-benzyloxycarbonylamino-3-tert-butoxycarbonyl-2-oxazolidone (306773-79-5)

Guidance literature:

With dmap; triethylamine; In tetrahydrofuran; at 5 - 10 ℃;

DOI:10.1021/jo000736e

Reference yield: 82.0%

(R)-4-benzyloxycarbonylamino-3-tert-butoxycarbonyl-2-oxazolidone (306773-79-5) → (R)-2-hydroxy-1-tert-butoxycarbonylaminoethylcarbamic acid benzyl ester (306773-80-8,306773-86-4)

Guidance literature:

With N-benzyl-trimethylammonium hydroxide; In tetrahydrofuran; methanol; at -40 ℃; for 0.666667h;

DOI:10.1021/jo000736e

Reference yield:

(R)-4-benzyloxycarbonylamino-3-tert-butoxycarbonyl-2-oxazolidone (306773-79-5) → (R)-tert-Butoxycarbonylamino-[5-((S)-2-carbamoyl-propyl)-2,4-dinitro-phenylamino]-acetic acid

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / benzyltrimethylammonium hydroxide / methanol; tetrahydrofuran / 0.67 h / -40 °C

2: 59 percent / pyridinium dichromate / dimethylformamide / 20 h / 20 °C

3: H₂ / Pd/C / methanol / 0.5 h / 0 °C / 51.72 Torr

4: Et₃N / methanol; acetone / 1 h / 40 °C

With dipyridinium dichromate; hydrogen; N-benzyl-trimethylammonium hydroxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetone; 1: Ring cleavage / 2: Oxidation / 3: Hydrogenolysis / 4: Substitution;

DOI:10.1021/jo000736e

upstream raw materials:

di-tert-butyl dicarbonate

(S)-4-benzyloxycarbonylamino-2-oxazolidone

Downstream raw materials:

(R)-2-hydroxy-1-tert-butoxycarbonylaminoethylcarbamic acid benzyl ester

(R)-benzyloxycarbonylamino-tert-butoxycarbonylaminoacetic acid