(2S,3R,4R,5R)-2-(((tert-butyl(dimethyl)silyl)oxy)methyl)-4-(dimethyl(phenyl)silyl)-5-((dimethyl(phenyl)silyl)methyl)-1-tosylpyrrolidin-3-ol

Base Information

• Chemical Name: (2S,3R,4R,5R)-2-(((tert-butyl(dimethyl)silyl)oxy)methyl)-4-(dimethyl(phenyl)silyl)-5-((dimethyl(phenyl)silyl)methyl)-1-tosylpyrrolidin-3-ol
• CAS No.: 912966-23-5
• Molecular Formula: C₃₅H₅₃NO₄SSi₃
• Molecular Weight: 668.133
• Mol file: 912966-23-5.mol

Synonyms:(2S,3R,4R,5R)-2-(((tert-butyl(dimethyl)silyl)oxy)methyl)-4-(dimethyl(phenyl)silyl)-5-((dimethyl(phenyl)silyl)methyl)-1-tosylpyrrolidin-3-ol

Chemical Property of (2S,3R,4R,5R)-2-(((tert-butyl(dimethyl)silyl)oxy)methyl)-4-(dimethyl(phenyl)silyl)-5-((dimethyl(phenyl)silyl)methyl)-1-tosylpyrrolidin-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,5R)-2-(((tert-butyl(dimethyl)silyl)oxy)methyl)-4-(dimethyl(phenyl)silyl)-5-((dimethyl(phenyl)silyl)methyl)-1-tosylpyrrolidin-3-ol

There total 2 articles about (2S,3R,4R,5R)-2-(((tert-butyl(dimethyl)silyl)oxy)methyl)-4-(dimethyl(phenyl)silyl)-5-((dimethyl(phenyl)silyl)methyl)-1-tosylpyrrolidin-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: 58.0%

1,3-bis(dimethylphenylsilyl)propene + N-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-formyl-ethyl]-4-methyl-benzenesulfonamide (209266-22-8) → (2S,3R,4R,5R)-2-(((tert-butyl(dimethyl)silyl)oxy)methyl)-4-(dimethyl(phenyl)silyl)-5-((dimethyl(phenyl)silyl)methyl)-1-tosylpyrrolidin-3-ol (912966-23-5)

Guidance literature:

With methylaluminum dichloride; In hexane; dichloromethane; at -78 ℃; for 2h; optical yield given as %de; stereoselective reaction; Inert atmosphere;

DOI:10.1002/chem.200701776

Reference yield: 57.0%

N-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-formyl-ethyl]-4-methyl-benzenesulfonamide (209266-22-8) + trans-1-dimethyl(phenyl)silyl-3-dimethy(phenyl)silylpropene (347374-00-9) → (2S,3R,4R,5R)-2-(((tert-butyl(dimethyl)silyl)oxy)methyl)-4-(dimethyl(phenyl)silyl)-5-((dimethyl(phenyl)silyl)methyl)-1-tosylpyrrolidin-3-ol (912966-23-5)

Guidance literature:

With methylaluminum dichloride; In hexane; dichloromethane; at -78 ℃;

DOI:10.1021/ja0647102

Reference yield: 96.0%

(2S,3R,4R,5R)-2-(((tert-butyl(dimethyl)silyl)oxy)methyl)-4-(dimethyl(phenyl)silyl)-5-((dimethyl(phenyl)silyl)methyl)-1-tosylpyrrolidin-3-ol (912966-23-5) → (2S,3R,4R,5R)-2-(hydroxymethyl)-4-[dimethyl(phenyl)silyl]-5-{[dimethyl(phenyl)silyl]methyl}-1-tosylpyrrolidin-3-ol (918107-49-0)

Guidance literature:

With water; acetic acid; In tetrahydrofuran; at 20 ℃; for 15h;

DOI:10.1002/chem.200701776

upstream raw materials:

N-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-formyl-ethyl]-4-methyl-benzenesulfonamide

trans-1-dimethyl(phenyl)silyl-3-dimethy(phenyl)silylpropene

Downstream raw materials:

(2S,3R,4R,5R)-2-(hydroxymethyl)-4-[dimethyl(phenyl)silyl]-5-{[dimethyl(phenyl)silyl]methyl}-1-tosylpyrrolidin-3-ol

(2S,3R,4R,5R)-2,5-bis(hydroxymethyl)-1-tosylpyrrolidine-3,4-diol