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

Base Information

• Chemical Name: (E)-(4S,5R)-6-(tert-Butyl-diphenyl-silanyloxy)-4-methanesulfonyloxy-2,5-dimethyl-hex-2-enoic acid methyl ester
• CAS No.: 203782-84-7
• Molecular Formula: C₂₆H₃₆O₆SSi
• Molecular Weight: 504.72
• Mol file: 203782-84-7.mol

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

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

There total 7 articles about (E)-(4S,5R)-6-(tert-Butyl-diphenyl-silanyloxy)-4-methanesulfonyloxy-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: 86.0%

methanesulfonyl chloride (124-63-0) + (E)-(4S,5R)-6-(tert-Butyl-diphenyl-silanyloxy)-4-hydroxy-2,5-dimethyl-hex-2-enoic acid methyl ester (203782-83-6) → (E)-(4S,5R)-6-(tert-Butyl-diphenyl-silanyloxy)-4-methanesulfonyloxy-2,5-dimethyl-hex-2-enoic acid methyl ester (203782-84-7)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 0 ℃; for 24h;

DOI:10.1021/jo9721397

Reference yield:

(4S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-penten-1-ol (127665-68-3) → (E)-(4S,5R)-6-(tert-Butyl-diphenyl-silanyloxy)-4-methanesulfonyloxy-2,5-dimethyl-hex-2-enoic acid methyl ester (203782-84-7)

Guidance literature:

Multi-step reaction with 7 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

6: 83 percent / Na₂CO₃ / methanol / 8 h / Ambient temperature

7: 86 percent / pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / 0 °C

With pyridine; tert.-butylhydroperoxide; dmap; sodium carbonate; D-(-)-diisopropyl tartrate; ammonium chloride; potassium iodide; zinc; In methanol; 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)-6-(tert-Butyl-diphenyl-silanyloxy)-4-methanesulfonyloxy-2,5-dimethyl-hex-2-enoic acid methyl ester (203782-84-7)

Guidance literature:

Multi-step reaction with 6 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

5: 83 percent / Na₂CO₃ / methanol / 8 h / Ambient temperature

6: 86 percent / pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / 0 °C

With pyridine; dmap; sodium carbonate; ammonium chloride; potassium iodide; zinc; In methanol; dichloromethane;

DOI:10.1021/jo9721397

upstream raw materials:

methanesulfonyl chloride

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

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

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

(3S,4E,6S)-3,6-dimethyl-7-(p-tolylsulfonyloxy)-3-(tolylsulfonyloxymethyl)hepta-1,4-diene

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