(2S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-(but-3-enyl)-1-p-toluenesulfonylpyrrolidine

Base Information

Chemical Name:(2S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-(but-3-enyl)-1-p-toluenesulfonylpyrrolidine
CAS No.:716336-80-0
Molecular Formula:C₃₂H₄₁NO₃SSi
Molecular Weight:547.834
Hs Code.:

Synonyms:(2S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-(but-3-enyl)-1-p-toluenesulfonylpyrrolidine

Suppliers and Price of (2S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-(but-3-enyl)-1-p-toluenesulfonylpyrrolidine

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-(but-3-enyl)-1-p-toluenesulfonylpyrrolidine

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (2S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-(but-3-enyl)-1-p-toluenesulfonylpyrrolidine

There total 8 articles about (2S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-(but-3-enyl)-1-p-toluenesulfonylpyrrolidine 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: 98.0%

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

: 1779-49-3
Methyltriphenylphosphonium bromide

: 716336-80-0
(2S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-(but-3-enyl)-1-p-toluenesulfonylpyrrolidine

Guidance literature:: Methyltriphenylphosphonium bromide; With potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 0.333333h;

3-[(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionaldehyde; In tetrahydrofuran; dichloromethane; at 0 ℃; for 14h;
DOI:10.1016/j.tet.2006.05.088

Reference yield: 77.0%

: 1779-49-3
Methyltriphenylphosphonium bromide

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

: 716336-80-0
(2S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-(but-3-enyl)-1-p-toluenesulfonylpyrrolidine

Guidance literature:: 3-((2S,5R)-2-(tert-butyldiphenylsilyloxymethyl)-1-p-toluenesulfonylpyrrolidin-5-yl)-propan-1-ol;

Methyltriphenylphosphonium bromide; With potassium tert-butylate; Further stages.;
DOI:10.1016/j.tetlet.2004.03.171

Reference yield:

: 716336-76-4
(S)-5-(3-(benzyloxy)propyl)-2-(tert-butyldiphenylsilyloxymethyl)-3,4-dihydro-2H-pyrrole

: 716336-80-0
(2S,5S)-2-(tert-butyldiphenylsilyloxymethyl)-5-(but-3-enyl)-1-p-toluenesulfonylpyrrolidine

Guidance literature:: Multi-step reaction with 5 steps

1.1: 92 percent / hydrogen / PtO₂ / ethanol / 1 h / 20 °C / 760 Torr

2.1: 96 percent / Et₃N; DMAP / CH₂Cl₂ / 14 h / 20 °C

3.1: 95 percent / hydrogen / Pd(OH)2/C / ethanol / 62 h / 20 °C / 760 Torr

4.1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

5.1: tBuOK / tetrahydrofuran / 0.33 h / 20 °C

5.2: 98 percent / tetrahydrofuran; CH₂Cl₂ / 14 h / 0 °C

With dmap; potassium tert-butylate; hydrogen; Dess-Martin periodane; triethylamine; platinum(IV) oxide; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; 4.1: Dess-Martin oxidation / 5.2: Wittig reaction;
DOI:10.1016/j.tet.2006.05.088