(2S,3S)-4-chloro-3-(2,4-difluorophenyl)-3-((trimethylsilyl)-oxy)butan-2-ol

Base Information

• Chemical Name: (2S,3S)-4-chloro-3-(2,4-difluorophenyl)-3-((trimethylsilyl)-oxy)butan-2-ol
• CAS No.: 1610930-73-8
• Molecular Formula: C₁₃H₁₉ClF₂O₂Si
• Molecular Weight: 308.828
• Mol file: 1610930-73-8.mol

Synonyms:(2S,3S)-4-chloro-3-(2,4-difluorophenyl)-3-((trimethylsilyl)-oxy)butan-2-ol

Chemical Property of (2S,3S)-4-chloro-3-(2,4-difluorophenyl)-3-((trimethylsilyl)-oxy)butan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-4-chloro-3-(2,4-difluorophenyl)-3-((trimethylsilyl)-oxy)butan-2-ol

There total 3 articles about (2S,3S)-4-chloro-3-(2,4-difluorophenyl)-3-((trimethylsilyl)-oxy)butan-2-ol 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: 57.0%

3-chloro-2-(2,4-difluorophenyl)-2-(trimethylsilanyloxy)propionaldehyde (861718-85-6) + methylmagnesium bromide (75-16-1) → (2R,3S)-4-chloro-3-(2,4-difluorophenyl)-3-((trimethylsilyl)-oxy)butan-2-ol (1584144-36-4) + (2S,3S)-4-chloro-3-(2,4-difluorophenyl)-3-((trimethylsilyl)-oxy)butan-2-ol (1610930-73-8)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 0.583333h; Inert atmosphere;

DOI:10.1021/jo500369y

Reference yield:

2-chloro-1-(2,4-dichlorophenyl)ethanone (51336-94-8) → (2S,3S)-4-chloro-3-(2,4-difluorophenyl)-3-((trimethylsilyl)-oxy)butan-2-ol (1610930-73-8)

Guidance literature:

Multi-step reaction with 3 steps

1: C₆H₁₈NSi₂^(1-)*Gd⁽¹⁺⁾; 1,5-anhydro-2,6-dideoxy-3-O-(4,5-difluoro-2-hydroxyphenyl)-6-(diphenylphosphinyl)-D-arabino-hexitol / -30 °C / Inert atmosphere

2: diisobutylaluminium hydride / toluene / -78 °C / Inert atmosphere

3: tetrahydrofuran / 0.58 h / -78 °C / Inert atmosphere

With C₆H₁₈NSi₂^(1-)*Gd⁽¹⁺⁾; diisobutylaluminium hydride; 1,5-anhydro-2,6-dideoxy-3-O-(4,5-difluoro-2-hydroxyphenyl)-6-(diphenylphosphinyl)-D-arabino-hexitol; In tetrahydrofuran; toluene;

DOI:10.1021/jo500369y

Reference yield:

(S)-3-chloro-2-(2,4-difluorophenyl)-2-((trimethylsilyl)oxy)propanenitrile (861718-83-4) → (2S,3S)-4-chloro-3-(2,4-difluorophenyl)-3-((trimethylsilyl)-oxy)butan-2-ol (1610930-73-8)

Guidance literature:

Multi-step reaction with 2 steps

1: diisobutylaluminium hydride / toluene / -78 °C / Inert atmosphere

2: tetrahydrofuran / 0.58 h / -78 °C / Inert atmosphere

With diisobutylaluminium hydride; In tetrahydrofuran; toluene;

DOI:10.1021/jo500369y

upstream raw materials:

3-chloro-2-(2,4-difluorophenyl)-2-(trimethylsilanyloxy)propionaldehyde

methylmagnesium bromide

2-chloro-1-(2,4-dichlorophenyl)ethanone

(S)-3-chloro-2-(2,4-difluorophenyl)-2-((trimethylsilyl)oxy)propanenitrile

Downstream raw materials:

(2S,3R)-1-chloro-2-(2,4-difluorophenyl)butane-2,3-diol

(1R)-1-<(2R)-2-(2,4-difluorophenyl)-2-oxiranyl>ethanol