(E)-(2R,3S)-1-(tert-Butyl-diphenyl-silanyloxy)-3-methoxymethoxy-hex-4-en-2-ol

Base Information

• Chemical Name: (E)-(2R,3S)-1-(tert-Butyl-diphenyl-silanyloxy)-3-methoxymethoxy-hex-4-en-2-ol
• CAS No.: 184691-03-0
• Molecular Formula: C₂₄H₃₄O₄Si
• Molecular Weight: 414.617
• Mol file: 184691-03-0.mol

Synonyms:(E)-(2R,3S)-1-(tert-Butyl-diphenyl-silanyloxy)-3-methoxymethoxy-hex-4-en-2-ol

Chemical Property of (E)-(2R,3S)-1-(tert-Butyl-diphenyl-silanyloxy)-3-methoxymethoxy-hex-4-en-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(2R,3S)-1-(tert-Butyl-diphenyl-silanyloxy)-3-methoxymethoxy-hex-4-en-2-ol

There total 3 articles about (E)-(2R,3S)-1-(tert-Butyl-diphenyl-silanyloxy)-3-methoxymethoxy-hex-4-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: 89.0%

(tert-butyldiphenylsilanyloxy)acetaldehyde (115869-43-7) + (1S,2E)-1-(tri-n-butylstannyl)-1-(methoxymethoxy)-2-butene (84510-37-2,131433-64-2,131433-65-3) → (E)-(2R,3S)-1-(tert-Butyl-diphenyl-silanyloxy)-3-methoxymethoxy-hex-4-en-2-ol (184691-03-0)

Guidance literature:

With indium(III) chloride; In ethyl acetate; -78 deg C to room temperature;

DOI:10.1021/jo961671b

Reference yield:

2-[(tert-butyldiphenylsilyl)oxy]ethanol (138499-16-8) → (E)-(2R,3S)-1-(tert-Butyl-diphenyl-silanyloxy)-3-methoxymethoxy-hex-4-en-2-ol (184691-03-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 15 min, 2.) -78 deg C to room temperature

2: 89 percent / InCl₃ / ethyl acetate / -78 deg C to room temperature

With indium(III) chloride; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; ethyl acetate;

DOI:10.1021/jo961671b

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (E)-(2R,3S)-1-(tert-Butyl-diphenyl-silanyloxy)-3-methoxymethoxy-hex-4-en-2-ol (184691-03-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / NaH / tetrahydrofuran / 1.) 0 deg C to room temperature, 40 min, 2.) room temperature, 16 h

2: 89 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 15 min, 2.) -78 deg C to room temperature

3: 89 percent / InCl₃ / ethyl acetate / -78 deg C to room temperature

With indium(III) chloride; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1021/jo961671b

upstream raw materials:

(tert-butyldiphenylsilanyloxy)acetaldehyde

(1S,2E)-1-(tri-n-butylstannyl)-1-(methoxymethoxy)-2-butene

2-[(tert-butyldiphenylsilyl)oxy]ethanol

tert-butylchlorodiphenylsilane

Downstream raw materials:

C₃₀H₄₈O₄Si₂

(2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxy)-2-methoxymethoxy-butyraldehyde

(E)-(2R,3S,4R,5R)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxy)-3-methoxymethoxy-oct-6-en-4-ol

C₄₄H₈₀O₆Si₄