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

Base Information

• Chemical Name: (2S,3R,4R,5R)-2,5-bis(hydroxymethyl)-1-tosylpyrrolidine-3,4-diol
• CAS No.: 912966-26-8
• Molecular Formula: C₁₃H₁₉NO₆S
• Molecular Weight: 317.363
• Mol file: 912966-26-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (2S,3R,4R,5R)-2,5-bis(hydroxymethyl)-1-tosylpyrrolidine-3,4-diol 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: 54.0%

(2S,3R,4R,5R)-2-(hydroxymethyl)-4-[dimethyl(phenyl)silyl]-5-{[dimethyl(phenyl)silyl]methyl}-1-tosylpyrrolidin-3-ol (918107-49-0) → (2S,3R,4R,5R)-2,5-bis(hydroxymethyl)-1-tosylpyrrolidine-3,4-diol (912966-26-8)

Guidance literature:

With peracetic acid; sodium acetate; potassium bromide; In acetic acid; at 20 - 40 ℃;

DOI:10.1021/ja0647102

Reference yield:

(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)-2,5-bis(hydroxymethyl)-1-tosylpyrrolidine-3,4-diol (912966-26-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / AcOH / tetrahydrofuran; H₂O / 18 h / 20 °C

2: 54 percent / KBr; AcOOH; NaOAc / acetic acid / 20 - 40 °C

With peracetic acid; sodium acetate; acetic acid; potassium bromide; In tetrahydrofuran; water; acetic acid; 2: Tamao-Fleming oxidation;

DOI:10.1021/ja0647102

Reference yield:

N-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-formyl-ethyl]-4-methyl-benzenesulfonamide (209266-22-8) → (2S,3R,4R,5R)-2,5-bis(hydroxymethyl)-1-tosylpyrrolidine-3,4-diol (912966-26-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 57 percent / MeAlCl₂ / CH₂Cl₂; hexane / -78 °C

2: 92 percent / AcOH / tetrahydrofuran; H₂O / 18 h / 20 °C

3: 54 percent / KBr; AcOOH; NaOAc / acetic acid / 20 - 40 °C

With peracetic acid; sodium acetate; methylaluminum dichloride; acetic acid; potassium bromide; In tetrahydrofuran; hexane; dichloromethane; water; acetic acid; 3: Tamao-Fleming oxidation;

DOI:10.1021/ja0647102

upstream 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-(((tert-butyl(dimethyl)silyl)oxy)methyl)-4-(dimethyl(phenyl)silyl)-5-((dimethyl(phenyl)silyl)methyl)-1-tosylpyrrolidin-3-ol

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

Downstream raw materials:

2,5-anhydro-2,5-imino-D-glucitol