(S)-4-benzyl-3-((2R,6R)-6-(tert-butyldimethylsilyloxy)-2-methyl-4-methylenenonanoyl)oxazolidin-2-one

Base Information

• Chemical Name: (S)-4-benzyl-3-((2R,6R)-6-(tert-butyldimethylsilyloxy)-2-methyl-4-methylenenonanoyl)oxazolidin-2-one
• CAS No.: 1420766-79-5
• Molecular Formula: C₂₇H₄₃NO₄Si
• Molecular Weight: 473.728
• Mol file: 1420766-79-5.mol

Synonyms:(S)-4-benzyl-3-((2R,6R)-6-(tert-butyldimethylsilyloxy)-2-methyl-4-methylenenonanoyl)oxazolidin-2-one

Chemical Property of (S)-4-benzyl-3-((2R,6R)-6-(tert-butyldimethylsilyloxy)-2-methyl-4-methylenenonanoyl)oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-benzyl-3-((2R,6R)-6-(tert-butyldimethylsilyloxy)-2-methyl-4-methylenenonanoyl)oxazolidin-2-one

There total 8 articles about (S)-4-benzyl-3-((2R,6R)-6-(tert-butyldimethylsilyloxy)-2-methyl-4-methylenenonanoyl)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: 75.0%

C14H29IOSi (1420767-01-6) + (S)-4-benzyl-3-propionyl-2-oxazolidinone (131685-53-5,101711-78-8) → (S)-4-benzyl-3-((2R,6R)-6-(tert-butyldimethylsilyloxy)-2-methyl-4-methylenenonanoyl)oxazolidin-2-one (1420766-79-5)

Guidance literature:

(S)-4-benzyl-3-propionyl-2-oxazolidinone; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

C₁₄H₂₉IOSi; In tetrahydrofuran; at -78 - -20 ℃; for 14h; Inert atmosphere;

DOI:10.1016/j.tet.2012.11.075

Reference yield: 60.0%

C14H29BrOSi + (S)-4-benzyl-3-propionyl-2-oxazolidinone (131685-53-5,101711-78-8) → (S)-4-benzyl-3-((2R,6R)-6-(tert-butyldimethylsilyloxy)-2-methyl-4-methylenenonanoyl)oxazolidin-2-one (1420766-79-5)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 - 0 ℃; for 18.75h;

DOI:10.1002/anie.201305467

Reference yield:

C13H28O2Si (1420766-95-5) → (S)-4-benzyl-3-((2R,6R)-6-(tert-butyldimethylsilyloxy)-2-methyl-4-methylenenonanoyl)oxazolidin-2-one (1420766-79-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: diethylamine / 1.5 h / 55 °C

1.2: 0.08 h / 20 °C

2.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -40 °C

3.1: 1H-imidazole; triphenylphosphine; iodine / tetrahydrofuran / 0.17 h / 0 °C

4.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

4.2: 14 h / -78 - -20 °C / Inert atmosphere

With 1H-imidazole; iodine; diisobutylaluminium hydride; diethylamine; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; toluene; 4.1: |Evans Aldol Reaction / 4.2: |Evans Aldol Reaction;

DOI:10.1016/j.tet.2012.11.075

upstream raw materials:

C₁₃H₂₈O₂Si

C₁₄H₂₈O₂Si

C₁₄H₂₉IOSi

(S)-4-benzyl-3-propionyl-2-oxazolidinone

Downstream raw materials:

(S)-((4R,8R)-9-(benzyloxy)-8-methyl-6-methylenenonan-4-yl)-6-((2S,3S,5R)-5-(2-(4-methoxybenzyloxy)ethyl)-3-methyltetrahydrofuran-2-yl)-2-methylhexanoate

((4R,8R)-9-(benzyloxy)-8-methyl-6-methylenenonan-4-yloxy)(tert-butyl)dimethylsilane

(4R,8R)-9-(benzyloxy)-8-methyl-6-methylenenonan-4-ol