(4R)-3-((2'R,3'S)-2'-bromo-3'-hydroxy-4'-methyl-4'-pentenoyl)-4-(phenylmethyl)-2-oxazolidinone

Base Information

• Chemical Name: (4R)-3-((2'R,3'S)-2'-bromo-3'-hydroxy-4'-methyl-4'-pentenoyl)-4-(phenylmethyl)-2-oxazolidinone
• CAS No.: 110905-25-4
• Molecular Formula: C₁₆H₁₈BrNO₄
• Molecular Weight: 368.227
• Mol file: 110905-25-4.mol

Synonyms:(4R)-3-((2'R,3'S)-2'-bromo-3'-hydroxy-4'-methyl-4'-pentenoyl)-4-(phenylmethyl)-2-oxazolidinone

Chemical Property of (4R)-3-((2'R,3'S)-2'-bromo-3'-hydroxy-4'-methyl-4'-pentenoyl)-4-(phenylmethyl)-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R)-3-((2'R,3'S)-2'-bromo-3'-hydroxy-4'-methyl-4'-pentenoyl)-4-(phenylmethyl)-2-oxazolidinone

There total 2 articles about (4R)-3-((2'R,3'S)-2'-bromo-3'-hydroxy-4'-methyl-4'-pentenoyl)-4-(phenylmethyl)-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:

(R)-4-(phenylmethyl)-2-oxazolidinone (40217-17-2,90719-32-7,120574-96-1,102029-44-7) → (4R)-3-((2'R,3'S)-2'-bromo-3'-hydroxy-4'-methyl-4'-pentenoyl)-4-(phenylmethyl)-2-oxazolidinone (110905-25-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / n-butyllithium / hexane; tetrahydrofuran / 0.17 h / -78 °C

2: 1.) triethylamine, di-n-butylboryl triflate / 1.) diethyl ether, room temperature, 1.5 h, 2.) diethyl ether, -78 deg C, 30 min, 0 deg C, 2 h

With n-butyllithium; di-n-butylboryl trifluoromethanesulfonate; triethylamine; In tetrahydrofuran; hexane;

DOI:10.1021/ja00257a041

Reference yield:

2-methylpropenal (78-85-3,25120-30-3) + (4R)-3-(bromoacetyl)-4-(phenylmethyl)-2-oxazolidinone (110905-24-3) → (4R)-3-((2'R,3'S)-2'-bromo-3'-hydroxy-4'-methyl-4'-pentenoyl)-4-(phenylmethyl)-2-oxazolidinone (110905-25-4)

Guidance literature:

With di-n-butylboryl trifluoromethanesulfonate; triethylamine; Yield given. Multistep reaction; 1.) diethyl ether, room temperature, 1.5 h, 2.) diethyl ether, -78 deg C, 30 min, 0 deg C, 2 h;

DOI:10.1021/ja00257a041

Reference yield: 82.0%

(4R)-3-((2'R,3'S)-2'-bromo-3'-hydroxy-4'-methyl-4'-pentenoyl)-4-(phenylmethyl)-2-oxazolidinone (110905-25-4) → (R)-4-Benzyl-3-((S)-3-hydroxy-2-imino-4-methyl-pent-4-enoyl)-oxazolidin-2-one + (4R)-3-((2'S,3'S)-2'-azido-3'-hydroxy-4'-methyl-4'-pentenoyl)-4-(phenylmethyl)-2-oxazolidinone (110905-26-5)

Guidance literature:

With sodium azide; In dimethyl sulfoxide; for 5h; Yields of byproduct given; Ambient temperature;

DOI:10.1021/ja00257a041

upstream raw materials:

2-methylpropenal

(4R)-3-(bromoacetyl)-4-(phenylmethyl)-2-oxazolidinone

(R)-4-(phenylmethyl)-2-oxazolidinone

Downstream raw materials:

(4R)-3-((2'S,3'S)-2'-azido-3'-hydroxy-4'-methyl-4'-pentenoyl)-4-(phenylmethyl)-2-oxazolidinone