(R)-3-((3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexanoyl)-4-phenyloxazolidin-2-one

Base Information

• Chemical Name: (R)-3-((3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexanoyl)-4-phenyloxazolidin-2-one
• CAS No.: 1351186-13-4
• Molecular Formula: C₃₃H₄₁NO₄Si
• Molecular Weight: 543.778
• Mol file: 1351186-13-4.mol

Synonyms:(R)-3-((3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexanoyl)-4-phenyloxazolidin-2-one

Chemical Property of (R)-3-((3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexanoyl)-4-phenyloxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-((3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexanoyl)-4-phenyloxazolidin-2-one

There total 2 articles about (R)-3-((3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexanoyl)-4-phenyloxazolidin-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:

(R)-3-((S,E)-6-(tert-butyldiphenylsilyloxy)-5-methylhex-2-enoyl)-4-phenyloxazolidin-2-one (1351186-11-2) + methylmagnesium bromide (75-16-1) → (R)-3-((3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexanoyl)-4-phenyloxazolidin-2-one (1351186-13-4) + (R)-3-((3R,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexanoyl)-4-phenyloxazolidin-2-one

Guidance literature:

methylmagnesium bromide; With copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; at -78 ℃; for 0.166667h; Inert atmosphere;

(R)-3-((S,E)-6-(tert-butyldiphenylsilyloxy)-5-methylhex-2-enoyl)-4-phenyloxazolidin-2-one; In tetrahydrofuran; at -78 - -40 ℃; optical yield given as %de; Inert atmosphere;

DOI:10.1021/jo201951s

Reference yield:

(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutanal (123444-68-8) + diethyl (R)-2-oxo-2-(2-oxo-4-phenyloxazolidin-3-yl)ethylphosphonate (227602-33-7) → (R)-3-((3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexanoyl)-4-phenyloxazolidin-2-one (1351186-13-4) + (R)-3-((3R,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexanoyl)-4-phenyloxazolidin-2-one

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

2.2: -78 - -40 °C / Inert atmosphere

With copper(I) bromide dimethylsulfide complex; sodium hexamethyldisilazane; In tetrahydrofuran; 1.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1021/jo201951s

Reference yield: 68.0%

(R)-3-((3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexanoyl)-4-phenyloxazolidin-2-one (1351186-13-4) → (3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexan-1-ol (128329-63-5)

Guidance literature:

With lithium borohydride; In methanol; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/jo201951s

upstream raw materials:

(R)-3-((S,E)-6-(tert-butyldiphenylsilyloxy)-5-methylhex-2-enoyl)-4-phenyloxazolidin-2-one

methylmagnesium bromide

(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutanal

diethyl (R)-2-oxo-2-(2-oxo-4-phenyloxazolidin-3-yl)ethylphosphonate

Downstream raw materials:

C₂₅H₃₈N₂O₄

(3R,4S,6S)-3,4,6-trimethyl-8-((R)-2-methylbutanamido)-N-((R)-1-(tritylthio)but-3-en-2-yl)octanamide

(3R,4S,6S)-8-((R)-N,2-dimethylbutanamido)-3,4,6-trimethyl-N-((R)-1-(tritylthio)but-3-en-2-yl)octanamide

(3R,4S,6S)-8-((R)-N,2-dimethylbutanamido)-3,4,6-trimethyl-N-((S)-1-(tritylthio)but-3-en-2-yl)octanamide