(1S,2R)-1-phenyl-1-(tert-butyldimethylsilyloxy)but-3-en-2-ol

Base Information

• Chemical Name: (1S,2R)-1-phenyl-1-(tert-butyldimethylsilyloxy)but-3-en-2-ol
• CAS No.: 675834-56-7
• Molecular Formula: C₁₆H₂₆O₂Si
• Molecular Weight: 278.467
• Mol file: 675834-56-7.mol

Synonyms:(1S,2R)-1-phenyl-1-(tert-butyldimethylsilyloxy)but-3-en-2-ol

Chemical Property of (1S,2R)-1-phenyl-1-(tert-butyldimethylsilyloxy)but-3-en-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R)-1-phenyl-1-(tert-butyldimethylsilyloxy)but-3-en-2-ol

There total 1 articles about (1S,2R)-1-phenyl-1-(tert-butyldimethylsilyloxy)but-3-en-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: 61.0%

(2S)-2-(tert-butyldimethylsilyloxy)-2-phenylacetaldehyde (133187-22-1) + vinylmagnesium chloride (3536-96-7) → (1S,2R)-1-phenyl-1-(tert-butyldimethylsilyloxy)but-3-en-2-ol (675834-56-7) + (1S,2S)-1-phenyl-1-(tert-butyldimethylsilyloxy)but-3-en-2-ol (675834-57-8)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 3h;

DOI:10.1016/j.tetasy.2003.10.026

Reference yield: 88.0%

(1S,2R)-1-phenyl-1-(tert-butyldimethylsilyloxy)but-3-en-2-ol (675834-56-7) → (1S,2R)-1-phenylbut-3-ene-1,2-diol (135414-96-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1016/j.tetasy.2003.10.026

Reference yield:

(1S,2R)-1-phenyl-1-(tert-butyldimethylsilyloxy)but-3-en-2-ol (675834-56-7) → [(4R,5S)-2,2-dimethyl-5-phenyl[1,3]dioxolan-4-yl]methanol (155749-26-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 88 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

2.1: 99 percent / Amberlyst(R)-15H / CH₂Cl₂ / 20 °C

3.1: ozone / CH₂Cl₂ / -78 - 20 °C

3.2: 68 percent / LiAlH₄ / tetrahydrofuran / 2 h / 20 °C

With Amberlyst(R)-15H; tetrabutyl ammonium fluoride; ozone; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetasy.2003.10.026

upstream raw materials:

(2S)-2-(tert-butyldimethylsilyloxy)-2-phenylacetaldehyde

vinylmagnesium chloride

Downstream raw materials:

(1S,2R)-1-phenylbut-3-ene-1,2-diol

[(4R,5S)-2,2-dimethyl-5-phenyl[1,3]dioxolan-4-yl]methanol

(4S,5R)-2,2-dimethyl-4-phenyl-5-ethenyl[1,3]dioxolane