(2S,2'R,3S)-3-(1-benzyl-5-oxopyrrolidin-2-yl)-3-(tert-butyldimethylsilanyloxy)-2-(triethylsilanyloxy)propionaldehyde

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Chemical Name:(2S,2'R,3S)-3-(1-benzyl-5-oxopyrrolidin-2-yl)-3-(tert-butyldimethylsilanyloxy)-2-(triethylsilanyloxy)propionaldehyde
CAS No.:445469-27-2
Molecular Formula:C₂₆H₄₅NO₄Si₂
Molecular Weight:491.819
Hs Code.:

Synonyms:(2S,2'R,3S)-3-(1-benzyl-5-oxopyrrolidin-2-yl)-3-(tert-butyldimethylsilanyloxy)-2-(triethylsilanyloxy)propionaldehyde

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Chemical Property of (2S,2'R,3S)-3-(1-benzyl-5-oxopyrrolidin-2-yl)-3-(tert-butyldimethylsilanyloxy)-2-(triethylsilanyloxy)propionaldehyde

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Technology Process of (2S,2'R,3S)-3-(1-benzyl-5-oxopyrrolidin-2-yl)-3-(tert-butyldimethylsilanyloxy)-2-(triethylsilanyloxy)propionaldehyde

There total 7 articles about (2S,2'R,3S)-3-(1-benzyl-5-oxopyrrolidin-2-yl)-3-(tert-butyldimethylsilanyloxy)-2-(triethylsilanyloxy)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: 98.0%

: 445469-26-1
(1'S,2'R,5R)-1-benzyl-5-[1-(tert-butyldimethylsilanyloxy)-2,3-bis-(triethylsilanyloxy)propyl]pyrrolidin-2-one

: 445469-27-2
(2S,2'R,3S)-3-(1-benzyl-5-oxopyrrolidin-2-yl)-3-(tert-butyldimethylsilanyloxy)-2-(triethylsilanyloxy)propionaldehyde

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -80 - 25 ℃;
DOI:10.1021/jo0257905

Reference yield:

: 141293-21-2
(1'S,4''R,5R)-1-(tert-butoxycarbonyl)-5-[(2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl]pyrrolidin-2-one

: 445469-27-2
(2S,2'R,3S)-3-(1-benzyl-5-oxopyrrolidin-2-yl)-3-(tert-butyldimethylsilanyloxy)-2-(triethylsilanyloxy)propionaldehyde

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 24 h / 20 °C

2: 90 percent / tert-butyldimethylsilyl trifluoromethanesulfonate; diisopropylethylamine / CH₂Cl₂ / 1 h / -15 °C

3: 88 percent / KH / tetrahydrofuran; various solvent(s) / 3 h / Heating

4: 95 percent / AcOH / H₂O / 6 h / 60 °C

5: 98 percent / 4-dimethylaminopyridine / pyridine / 2 h / 20 °C

6: 98 percent / oxalyl chloride; dimethylsulfoxide; triethylamine / CH₂Cl₂ / -80 - 25 °C

With 2,6-dimethylpyridine; dmap; oxalyl dichloride; t-butyldimethylsiyl triflate; potassium hydride; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; dichloromethane; water; 6: Swern oxidation;
DOI:10.1021/jo0257905

Reference yield:

: 141293-15-4
(1'S,2R,4''R)-2-[(2,2-dimethyl-[1,3]dioxolan-4-yl)hydroxymethyl]-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylic acid tert-butyl ester

: 445469-27-2
(2S,2'R,3S)-3-(1-benzyl-5-oxopyrrolidin-2-yl)-3-(tert-butyldimethylsilanyloxy)-2-(triethylsilanyloxy)propionaldehyde

Guidance literature:: Multi-step reaction with 7 steps

1: 98 percent / NiCl₂*6H₂O; NaBH₄ / methanol / 0.75 h / 0 °C

2: 95 percent / 2,6-lutidine / CH₂Cl₂ / 24 h / 20 °C

3: 90 percent / tert-butyldimethylsilyl trifluoromethanesulfonate; diisopropylethylamine / CH₂Cl₂ / 1 h / -15 °C

4: 88 percent / KH / tetrahydrofuran; various solvent(s) / 3 h / Heating

5: 95 percent / AcOH / H₂O / 6 h / 60 °C

6: 98 percent / 4-dimethylaminopyridine / pyridine / 2 h / 20 °C

7: 98 percent / oxalyl chloride; dimethylsulfoxide; triethylamine / CH₂Cl₂ / -80 - 25 °C

With 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; oxalyl dichloride; t-butyldimethylsiyl triflate; potassium hydride; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; nickel dichloride; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; 7: Swern oxidation;
DOI:10.1021/jo0257905