(3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-pent-1-en-3-ol

Base Information

• Chemical Name: (3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-pent-1-en-3-ol
• CAS No.: 200199-15-1
• Molecular Formula: C₂₂H₃₀O₂Si
• Molecular Weight: 354.565
• Mol file: 200199-15-1.mol

Synonyms:(3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-pent-1-en-3-ol

Chemical Property of (3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-pent-1-en-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-pent-1-en-3-ol

There total 6 articles about (3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-pent-1-en-3-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:

((2R,3R)-3-((R)-1-((tert-butyldiphenylsilyl)oxy)propan-2-yl)oxiran-2-yl)methanol (127665-69-4) → (3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-pent-1-en-3-ol (200199-15-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 40 h / Ambient temperature

2: 1.) KI, 2.) Zn, NH₄Cl / 1.) DMF, 55 deg C, 1.5 h, 2.) DMF, 0 deg C, 30 min,

With pyridine; dmap; ammonium chloride; potassium iodide; zinc; In dichloromethane;

DOI:10.1021/jo9721397

Reference yield:

(4S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-penten-1-ol (127665-68-3) → (3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-pent-1-en-3-ol (200199-15-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / diisopropyl D-tartrate, t-BuOOH / CH₂Cl₂; 2,2,4-trimethyl-pentane / 26 h / -20 °C

2: 74 percent / pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 40 h / Ambient temperature

3: 1.) KI, 2.) Zn, NH₄Cl / 1.) DMF, 55 deg C, 1.5 h, 2.) DMF, 0 deg C, 30 min,

With pyridine; tert.-butylhydroperoxide; dmap; D-(-)-diisopropyl tartrate; ammonium chloride; potassium iodide; zinc; In 2,2,4-trimethylpentane; dichloromethane;

DOI:10.1021/jo9721397

Reference yield:

(S)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol (95514-04-8,129029-85-2,120346-83-0) → (3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-pent-1-en-3-ol (200199-15-1)

Guidance literature:

Multi-step reaction with 2 steps

1: Dess-Martin periodinane / CH₂Cl₂ / 20 °C

2: tetrahydrofuran / -78 - 20 °C

With Dess-Martin periodane; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(01)02078-0

upstream raw materials:

Toluene-4-sulfonic acid (2R,3R)-3-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-oxiranylmethyl ester

(S)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol

(R)-methyl 3-(tert-butyl(diphenyl)silyloxy)-2-methylpropanoate

tert-butylchlorodiphenylsilane

Downstream raw materials:

(E)-(2S,5S)-6-(tert-Butyl-diphenyl-silanyloxy)-2,5-dimethyl-2-vinyl-hex-3-enoic acid methyl ester

Toluene-4-sulfonic acid (E)-(2S,5S)-6-(tert-butyl-diphenyl-silanyloxy)-2,5-dimethyl-2-vinyl-hex-3-enyl ester

(E)-(4S,5R)-6-(tert-Butyl-diphenyl-silanyloxy)-4-methanesulfonyloxy-2,5-dimethyl-hex-2-enoic acid methyl ester

(E)-(4S,5R)-4-Acetoxy-6-(tert-butyl-diphenyl-silanyloxy)-2,5-dimethyl-hex-2-enoic acid methyl ester