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

Base Information

• Chemical Name: (E)-(4S,5R)-4-Acetoxy-6-(tert-butyl-diphenyl-silanyloxy)-2,5-dimethyl-hex-2-enoic acid methyl ester
• CAS No.: 203782-82-5
• Molecular Formula: C₂₇H₃₆O₅Si
• Molecular Weight: 468.665
• Mol file: 203782-82-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

(4S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-penten-1-ol (127665-68-3) → (E)-(4S,5R)-4-Acetoxy-6-(tert-butyl-diphenyl-silanyloxy)-2,5-dimethyl-hex-2-enoic acid methyl ester (203782-82-5)

Guidance literature:

Multi-step reaction with 5 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,

4: 99 percent / pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / Ambient temperature

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:

((2R,3R)-3-((R)-1-((tert-butyldiphenylsilyl)oxy)propan-2-yl)oxiran-2-yl)methanol (127665-69-4) → (E)-(4S,5R)-4-Acetoxy-6-(tert-butyl-diphenyl-silanyloxy)-2,5-dimethyl-hex-2-enoic acid methyl ester (203782-82-5)

Guidance literature:

Multi-step reaction with 4 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,

3: 99 percent / pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / Ambient temperature

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

DOI:10.1021/jo9721397

Reference yield:

(3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-pent-1-en-3-ol (200199-15-1) → (E)-(4S,5R)-4-Acetoxy-6-(tert-butyl-diphenyl-silanyloxy)-2,5-dimethyl-hex-2-enoic acid methyl ester (203782-82-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; dmap; In dichloromethane;

DOI:10.1021/jo9721397

upstream raw materials:

methyl 2-(triphenylphosphoranylidene)propionate

Acetic acid (S)-1-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-allyl ester

(4S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-penten-1-ol

((2R,3R)-3-((R)-1-((tert-butyldiphenylsilyl)oxy)propan-2-yl)oxiran-2-yl)methanol

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)-(2S,5S)-6-(tert-Butyl-diphenyl-silanyloxy)-2,5-dimethyl-2-vinyl-hex-3-en-1-ol