3-[(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionaldehyde

Base Information

Chemical Name:3-[(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionaldehyde
CAS No.:916152-69-7
Molecular Formula:C₃₁H₃₉NO₄SSi
Molecular Weight:549.806
Hs Code.:

Synonyms:3-[(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionaldehyde

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Chemical Property of 3-[(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionaldehyde

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Technology Process of 3-[(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionaldehyde

There total 5 articles about 3-[(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionaldehyde 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: 99.0%

: 716336-79-7
3-((2S,5R)-2-(tert-butyldiphenylsilyloxymethyl)-1-p-toluenesulfonylpyrrolidin-5-yl)-propan-1-ol

: 916152-69-7
3-[(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionaldehyde

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1016/j.tet.2006.05.088

Reference yield:

: 916152-63-1
(2R,5S)-2-(3-Benzyloxy-propyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidine

: 916152-69-7
3-[(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1: 96 percent / Et₃N; DMAP / CH₂Cl₂ / 14 h / 20 °C

2: 95 percent / hydrogen / Pd(OH)2/C / ethanol / 62 h / 20 °C / 760 Torr

3: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

With dmap; hydrogen; Dess-Martin periodane; triethylamine; palladium dihydroxide; In ethanol; dichloromethane; 3: Dess-Martin oxidation;
DOI:10.1016/j.tet.2006.05.088

Reference yield:

: 916152-68-6
(2R,5S)-2-(3-Benzyloxy-propyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidine

: 916152-69-7
3-[(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionaldehyde

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / hydrogen / Pd(OH)2/C / ethanol / 62 h / 20 °C / 760 Torr

2: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

With hydrogen; Dess-Martin periodane; palladium dihydroxide; In ethanol; dichloromethane; 2: Dess-Martin oxidation;
DOI:10.1016/j.tet.2006.05.088