(2R,3R)-1-[(tert-butyldimethylsilyl)oxy]-3-phenyl-2-butanol

Base Information

• Chemical Name: (2R,3R)-1-[(tert-butyldimethylsilyl)oxy]-3-phenyl-2-butanol
• CAS No.: 197714-08-2
• Molecular Formula: C₁₆H₂₈O₂Si
• Molecular Weight: 280.483
• Mol file: 197714-08-2.mol

Synonyms:(2R,3R)-1-[(tert-butyldimethylsilyl)oxy]-3-phenyl-2-butanol

Chemical Property of (2R,3R)-1-[(tert-butyldimethylsilyl)oxy]-3-phenyl-2-butanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-1-[(tert-butyldimethylsilyl)oxy]-3-phenyl-2-butanol

There total 4 articles about (2R,3R)-1-[(tert-butyldimethylsilyl)oxy]-3-phenyl-2-butanol 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: 78.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (2R,3R)-3-phenyl-butane-1,2-diol (121840-97-9) → (2R,3R)-2-[(tert-butyldimethylsilyl)oxy]-3-phenyl-1-butanol + (2R,3R)-1-[(tert-butyldimethylsilyl)oxy]-3-phenyl-2-butanol (197714-08-2)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 24h;

DOI:10.1021/jo971178f

Reference yield:

(2E)-3-phenyl-2-propen-1-ol (4407-36-7) → (2R,3R)-1-[(tert-butyldimethylsilyl)oxy]-3-phenyl-2-butanol (197714-08-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: titanium(IV) isopropylate / dichloromethane / 0.5 h / -20 °C / Molecular sieve

1.2: 16 h / -20 °C / Molecular sieve

2.1: copper(l) iodide / diethyl ether / 0.33 h / -40 °C

2.2: 20 °C

3.1: 1H-imidazole / dichloromethane / 0 - 35 °C

With 1H-imidazole; titanium(IV) isopropylate; copper(l) iodide; In diethyl ether; dichloromethane; 1.1: |Sharpless Asymmetric Epoxidation / 1.2: |Sharpless Asymmetric Epoxidation;

DOI:10.1055/s-0039-1691503

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) + (2R,3R)-3-phenyl-butane-1,2-diol (121840-97-9) → (2R,3R)-1-[(tert-butyldimethylsilyl)oxy]-3-phenyl-2-butanol (197714-08-2)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 0 - 35 ℃;

DOI:10.1055/s-0039-1691503

upstream raw materials:

tert-butyldimethylsilyl chloride

(2R,3R)-3-phenyl-butane-1,2-diol

(2S,3S)-2,3-epoxy-3-phenyl-1-propanol

(2E)-3-phenyl-2-propen-1-ol

Downstream raw materials:

(2R,3R)-1-[(tert-butyldimethylsilyl)oxy]-2-(methanesulfonyloxy)-3-phenylbutane

(2S,3R)-1-[(tert-butyldimethylsilyl)oxy]-3-phenyl-2-[(p-nitrobenzoyl)oxy]butane

(βR)-N-(tert-butoxycarbonyl)-β-methyl-L-phenylalanine

(2R,3R)-2-[(tert-butoxycarbonyl)amino]-3-phenylbutanoic acid