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

Base Information

• Chemical Name: Toluene-4-sulfonic acid (3R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl ester
• CAS No.: 216692-09-0
• Molecular Formula: C₃₅H₄₁NO₆S₂Si
• Molecular Weight: 663.931
• Mol file: 216692-09-0.mol

Synonyms:Toluene-4-sulfonic acid (3R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl ester

Chemical Property of Toluene-4-sulfonic acid (3R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (3R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl ester

There total 4 articles about Toluene-4-sulfonic acid (3R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl 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: 100.0%

(2S,4R)-2-(hydroxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine (118329-82-1) + tert-butylchlorodiphenylsilane (58479-61-1) → Toluene-4-sulfonic acid (3R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl ester (216692-09-0)

Guidance literature:

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

DOI:10.1016/S0040-4020(98)00821-7

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → Toluene-4-sulfonic acid (3R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl ester (216692-09-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / Et₃N, DMAP / CH₂Cl₂ / 48 h / Ambient temperature

2: LiBH₄ / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 1 h

3: 100 percent / imidazole, DMAP / CH₂Cl₂ / 18 h

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

DOI:10.1016/S0040-4020(98)00821-7

Reference yield:

N,O-ditosyl-trans-4-hydroxy-L-proline methyl ester (16257-73-1) → Toluene-4-sulfonic acid (3R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl ester (216692-09-0)

Guidance literature:

Multi-step reaction with 2 steps

1: LiBH₄ / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 1 h

2: 100 percent / imidazole, DMAP / CH₂Cl₂ / 18 h

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

DOI:10.1016/S0040-4020(98)00821-7

upstream raw materials:

(2S,4R)-2-(hydroxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine

tert-butylchlorodiphenylsilane

L-4-hydroxyproline methyl ester hydrochloride

N,O-ditosyl-trans-4-hydroxy-L-proline methyl ester

Downstream raw materials:

(2S,4S)-4-Azido-2-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidine

5-Ethyl-1-[(3S,5S)-5-hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-1H-pyrimidine-2,4-dione

Acetic acid (2S,4S)-4-(5-ethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester

Acetic acid (2S,4S)-4-[5-((E)-2-bromo-vinyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester