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

Base Information

• Chemical Name: (2S,4S)-4-Azido-2-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidine
• CAS No.: 216692-17-0
• Molecular Formula: C₂₈H₃₄N₄O₃SSi
• Molecular Weight: 534.754
• Mol file: 216692-17-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about (2S,4S)-4-Azido-2-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidine 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: 87.0%

Toluene-4-sulfonic acid (3R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl ester (216692-09-0) → (2S,4S)-4-Azido-2-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidine (216692-17-0)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; 1.) 70 deg C, 5 h, 2.) room temperature, 18 h;

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

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → (2S,4S)-4-Azido-2-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidine (216692-17-0)

Guidance literature:

Multi-step reaction with 4 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

4: 87 percent / aq. NaN₃ / dimethylformamide / 1.) 70 deg C, 5 h, 2.) room temperature, 18 h

With 1H-imidazole; dmap; lithium borohydride; sodium azide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

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

Reference yield:

(2S,4R)-2-(hydroxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine (118329-82-1) → (2S,4S)-4-Azido-2-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidine (216692-17-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / imidazole, DMAP / CH₂Cl₂ / 18 h

2: 87 percent / aq. NaN₃ / dimethylformamide / 1.) 70 deg C, 5 h, 2.) room temperature, 18 h

With 1H-imidazole; dmap; sodium azide; In dichloromethane; N,N-dimethyl-formamide;

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

upstream raw materials:

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

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

L-4-hydroxyproline methyl ester hydrochloride

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

Downstream raw materials:

(3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-ylamine

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