5-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol

Base Information

• Chemical Name: 5-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol
• CAS No.: 906065-74-5
• Molecular Formula: C₂₈H₃₅NO₄SSi
• Molecular Weight: 509.742
• Mol file: 906065-74-5.mol

Synonyms:5-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol

Chemical Property of 5-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol

There total 6 articles about 5-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-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: 47.0%

(2R,4S)-2-(Hydroxymethyl)-4-hydroxy-1-(4-tolylsulfonyl)pyrrolidine (116143-08-9) + tert-butylchlorodiphenylsilane (58479-61-1) → 5-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol (906065-74-5)

Guidance literature:

With 1H-imidazole; dmap; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1016/j.bmcl.2006.04.085

Reference yield:

allo-1-(4-tolylsulfonyl)-4-<<(4-methylphenyl)sulfonyl>oxy>-D-proline ethyl ester (116143-05-6) → 5-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol (906065-74-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / toluene / 12 h / Heating

2: 76 percent / LiBH₄ / tetrahydrofuran / 12 h / 20 °C

3: 47 percent / imidazole; DMAP / CH₂Cl₂ / 18 h / 20 °C

With 1H-imidazole; dmap; lithium borohydride; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/j.bmcl.2006.04.085

Reference yield:

(2R,4R)-2-ethoxycarbonyl-4-hydroxypyrrolidine hydrochloride (77449-99-1) → 5-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol (906065-74-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 68 percent / Et₃N; Py / 18 h / -5 - 20 °C

2: 75 percent / toluene / 12 h / Heating

3: 76 percent / LiBH₄ / tetrahydrofuran / 12 h / 20 °C

4: 47 percent / imidazole; DMAP / CH₂Cl₂ / 18 h / 20 °C

With pyridine; 1H-imidazole; dmap; lithium borohydride; triethylamine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/j.bmcl.2006.04.085

upstream raw materials:

(2R,4S)-2-(Hydroxymethyl)-4-hydroxy-1-(4-tolylsulfonyl)pyrrolidine

tert-butylchlorodiphenylsilane

(2R,4R)-2-ethoxycarbonyl-4-hydroxypyrrolidine hydrochloride

4-(acetyloxy)-1-<(4-methylphenyl)sulfonyl>-D-proline ethyl ester

Downstream raw materials:

toluene-4-sulfonic acid 5-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl ester

cis-4-(6-amino-9H-purin-9-yl)-D-prolinol