(R)-4-benzyl-3-((S,E)-2,4-dimethylhex-4-enoyl)oxazolidin-2-one

Base Information

• Chemical Name: (R)-4-benzyl-3-((S,E)-2,4-dimethylhex-4-enoyl)oxazolidin-2-one
• CAS No.: 936946-32-6
• Molecular Formula: C₁₈H₂₃NO₃
• Molecular Weight: 301.386
• Mol file: 936946-32-6.mol

Synonyms:(R)-4-benzyl-3-((S,E)-2,4-dimethylhex-4-enoyl)oxazolidin-2-one

Chemical Property of (R)-4-benzyl-3-((S,E)-2,4-dimethylhex-4-enoyl)oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-benzyl-3-((S,E)-2,4-dimethylhex-4-enoyl)oxazolidin-2-one

There total 6 articles about (R)-4-benzyl-3-((S,E)-2,4-dimethylhex-4-enoyl)oxazolidin-2-one 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: 89.0%

tiglyl bromide (57253-30-2) + (3R)-3-propionyl-4-benzyloxazolidin-2-one (101711-78-8,131685-53-5) → (R)-4-benzyl-3-((S,E)-2,4-dimethylhex-4-enoyl)oxazolidin-2-one (936946-32-6)

Guidance literature:

(3R)-3-propionyl-4-benzyloxazolidin-2-one; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃;

tiglyl bromide; In tetrahydrofuran; for 16h; stereoselective reaction;

DOI:10.1021/ol8018105

Reference yield: 72.0%

(3R)-3-propionyl-4-benzyloxazolidin-2-one (101711-78-8,131685-53-5) + (E)-1-iodo-2-methyl-but-2-ene (66702-98-5) → (R)-4-benzyl-3-((S,E)-2,4-dimethylhex-4-enoyl)oxazolidin-2-one (936946-32-6)

Guidance literature:

(3R)-3-propionyl-4-benzyloxazolidin-2-one; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

(E)-1-iodo-2-methyl-but-2-ene; In tetrahydrofuran; at -78 - -30 ℃; Inert atmosphere;

DOI:10.1021/ol2017802

Reference yield:

(E)-2-methyl-2-buten-1-ol (497-02-9) → (R)-4-benzyl-3-((S,E)-2,4-dimethylhex-4-enoyl)oxazolidin-2-one (936946-32-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 52 percent / PBr₃; pyridine

2: 83 percent / NaHMDS

With pyridine; sodium hexamethyldisilazane; phosphorus tribromide; 2: Evans alkylation;

DOI:10.1016/j.tetlet.2007.02.081

upstream raw materials:

tiglyl bromide

(3R)-3-propionyl-4-benzyloxazolidin-2-one

Tiglic acid

(E)-2-methyl-2-buten-1-ol

Downstream raw materials:

C₃₀H₄₇NO₅Si

C₂₄H₃₅NO₅

(2'S,3'R,4'R,5'S,6'S,8E,4S)-3-[(5-[tert-butyldimethylsilyloxy]-3-triethylsilyloxyl-2,4,6,8-tetramethyl-1-oxo-dec-8-enyl)-4-(phenylmethyl)]-2-oxazolidinone

(2'S,3'R,4'S,5'S,6'S,8E,4S)-3-[(5-[tert-butyldimethylsilyloxy]-3-hydroxyl-2,4,6,8-tetramethyl-1-oxo-dec-8-enyl)-4-(phenylmethyl)]-2-oxazolidinone