(S)-3-(6-azido-(2R)-benzyl-1-oxohexyl)-4-benzyl-2-oxazolidinone

Base Information

• Chemical Name: (S)-3-(6-azido-(2R)-benzyl-1-oxohexyl)-4-benzyl-2-oxazolidinone
• CAS No.: 286964-96-3
• Molecular Formula: C₂₃H₂₆N₄O₃
• Molecular Weight: 406.484
• Mol file: 286964-96-3.mol

Synonyms:(S)-3-(6-azido-(2R)-benzyl-1-oxohexyl)-4-benzyl-2-oxazolidinone

Chemical Property of (S)-3-(6-azido-(2R)-benzyl-1-oxohexyl)-4-benzyl-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-(6-azido-(2R)-benzyl-1-oxohexyl)-4-benzyl-2-oxazolidinone

There total 4 articles about (S)-3-(6-azido-(2R)-benzyl-1-oxohexyl)-4-benzyl-2-oxazolidinone 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: 73.0%

benzyl bromide (100-39-0) + (4S)-3-(6-azido-1-oxohexyl)-4-benzyl-2-oxazolidinone (286964-95-2) → (S)-3-(6-azido-(2R)-benzyl-1-oxohexyl)-4-benzyl-2-oxazolidinone (286964-96-3)

Guidance literature:

With sodium hexamethyldisilazane;

DOI:10.1021/ol005618s

Reference yield:

(S)-4-benzyl-3-(6-bromo-1-oxohexyl)-2-oxazolidinone (203739-34-8) → (S)-3-(6-azido-(2R)-benzyl-1-oxohexyl)-4-benzyl-2-oxazolidinone (286964-96-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaN₃ / dimethylformamide / 19 h / 20 °C

2.1: NaN(TMS)2 / tetrahydrofuran / 0.75 h / -78 °C

2.2: 54 percent / tetrahydrofuran / 2 h / 0 °C

With sodium azide; sodium hexamethyldisilazane; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo001308b

Reference yield:

6-bromohexanoyl chloride (22809-37-6) → (S)-3-(6-azido-(2R)-benzyl-1-oxohexyl)-4-benzyl-2-oxazolidinone (286964-96-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

1.2: 76 percent / tetrahydrofuran; hexane / 6 h / 20 °C

2.1: NaN₃ / dimethylformamide / 19 h / 20 °C

3.1: NaN(TMS)2 / tetrahydrofuran / 0.75 h / -78 °C

3.2: 54 percent / tetrahydrofuran / 2 h / 0 °C

With n-butyllithium; sodium azide; sodium hexamethyldisilazane; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1021/jo001308b

upstream raw materials:

benzyl bromide

(4S)-3-(6-azido-1-oxohexyl)-4-benzyl-2-oxazolidinone

6-bromohexanoyl chloride

(S)-4-Benzyl-2-oxazolidinone

Downstream raw materials:

(2R)-6-N-(tert-butoxycarbonyl)amino-2-benzylhexanoyl-glycyl-glycine ethyl ester

(2R)-6-N-(tert-butoxycarbonyl)amino-2-benzylhexanoyl-glycyl-glycine

(2R)-6-azido-2-benzylhexanoyl-glycyl-glycine ethyl ester

(2R)-6-azido-2-benzylhexanoic acid