3-[(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionaldehyde

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Chemical Name:3-[(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionaldehyde
CAS No.:870246-70-1
Molecular Formula:C₂₀H₃₃NO₄SSi
Molecular Weight:411.638
Hs Code.:

Synonyms:3-[(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionaldehyde

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Chemical Property of 3-[(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionaldehyde

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Technology Process of 3-[(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionaldehyde

There total 9 articles about 3-[(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-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: 88.0%

: 870246-65-4
3-[(2R,4R)-1-(4-methylphenyl)sulfonyl-4-(t-butyldimethylsilanyloxy)pyrrolidin-2-yl]-propan-1-ol

: 870246-70-1
3-[(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionaldehyde

Guidance literature:: With Celite; pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 15h;
DOI:10.1016/j.tetlet.2005.09.024

Reference yield:

: 40216-83-9
L-4-hydroxyproline methyl ester hydrochloride

: 870246-70-1
3-[(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionaldehyde

Guidance literature:: Multi-step reaction with 8 steps

1: 2.93 g / triethylamine / CH₂Cl₂ / 10 h / 20 °C

2: 3.93 g / imidazole / dimethylformamide / 2 h / 20 °C

3: 3.47 g / NaBH₄; LiCl; MeOH / 12 h / 20 °C

4: 950 mg / oxalyl chloride; triethylamine; DMSO / CH₂Cl₂ / -78 - 20 °C

5: 1.06 g / CH₂Cl₂ / 5 h / 20 °C

6: 99 percent / H₂ / Pd/C / methanol / 10 h / 20 °C

7: 94 percent / LiAlH₄ / tetrahydrofuran / 3 h / 20 °C

8: 88 percent / pyridinium chlorochromate; Celite / CH₂Cl₂ / 15 h / 20 °C

With 1H-imidazole; methanol; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; Celite; hydrogen; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 4: Swern oxidation / 5: Wittig olefination;
DOI:10.1016/j.tetlet.2005.09.024

Reference yield:

: ethyl 3-[(2S,4R)-1-(4-methylphenyl)sulfonyl-4-(t-butyldimethylsilanyloxy)pyrrolidin-2-yl]-acrylate

: 870246-70-1
3-[(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1: 99 percent / H₂ / Pd/C / methanol / 10 h / 20 °C

2: 94 percent / LiAlH₄ / tetrahydrofuran / 3 h / 20 °C

3: 88 percent / pyridinium chlorochromate; Celite / CH₂Cl₂ / 15 h / 20 °C

With lithium aluminium tetrahydride; Celite; hydrogen; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/j.tetlet.2005.09.024