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

Base Information

• Chemical Name: Toluene-4-sulfonic acid (2R,3R)-3-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-oxiranylmethyl ester
• CAS No.: 200199-14-0
• Molecular Formula: C₂₉H₃₆O₅SSi
• Molecular Weight: 524.753
• Mol file: 200199-14-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about Toluene-4-sulfonic acid (2R,3R)-3-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-oxiranylmethyl 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: 74.0%

((2R,3R)-3-((R)-1-((tert-butyldiphenylsilyl)oxy)propan-2-yl)oxiran-2-yl)methanol (127665-69-4) + p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid (2R,3R)-3-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-oxiranylmethyl ester (200199-14-0)

Guidance literature:

With pyridine; dmap; In dichloromethane; for 40h; Ambient temperature;

DOI:10.1021/jo9721397

Reference yield:

(4S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-penten-1-ol (127665-68-3) → Toluene-4-sulfonic acid (2R,3R)-3-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-oxiranylmethyl ester (200199-14-0)

Guidance literature:

Multi-step reaction with 2 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

With pyridine; tert.-butylhydroperoxide; dmap; D-(-)-diisopropyl tartrate; In 2,2,4-trimethylpentane; dichloromethane;

DOI:10.1021/jo9721397

Reference yield:

Toluene-4-sulfonic acid (2R,3R)-3-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-oxiranylmethyl ester (200199-14-0) → (3S,4E,6S)-3,6-dimethyl-7-(p-tolylsulfonyloxy)-3-(tolylsulfonyloxymethyl)hepta-1,4-diene (112763-53-8)

Guidance literature:

Multi-step reaction with 10 steps

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

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

4: 83 percent / Na₂CO₃ / methanol / 8 h / Ambient temperature

5: 86 percent / pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / 0 °C

6: 75 percent / LiCl, ZnCl₂, CuCN / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) 0 deg C, 5 h

7: 82 percent / DIBAL / CH₂Cl₂; toluene / 0.5 h / -78 °C

8: 97 percent / pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h / Ambient temperature

9: Bu₄NF / tetrahydrofuran / 7 h / Ambient temperature

10: pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 14 h / 0 °C

With pyridine; dmap; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; sodium carbonate; ammonium chloride; potassium iodide; lithium chloride; zinc(II) chloride; zinc; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1021/jo9721397

upstream raw materials:

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

p-toluenesulfonyl chloride

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

Downstream raw materials:

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

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

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

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