(2S,4R)-2-[((R)-4-acetoxymethyl)thiazolidin-2-yl]-4-(tert-butyldimethylsilanyloxy)-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

Base Information

Chemical Name:(2S,4R)-2-[((R)-4-acetoxymethyl)thiazolidin-2-yl]-4-(tert-butyldimethylsilanyloxy)-1-(p-nitrobenzyloxycarbonyl)pyrrolidine
CAS No.:466651-70-7
Molecular Formula:C₂₄H₃₇N₃O₇SSi
Molecular Weight:539.725
Hs Code.:

Synonyms:(2S,4R)-2-[((R)-4-acetoxymethyl)thiazolidin-2-yl]-4-(tert-butyldimethylsilanyloxy)-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

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Chemical Property of (2S,4R)-2-[((R)-4-acetoxymethyl)thiazolidin-2-yl]-4-(tert-butyldimethylsilanyloxy)-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

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Technology Process of (2S,4R)-2-[((R)-4-acetoxymethyl)thiazolidin-2-yl]-4-(tert-butyldimethylsilanyloxy)-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

There total 3 articles about (2S,4R)-2-[((R)-4-acetoxymethyl)thiazolidin-2-yl]-4-(tert-butyldimethylsilanyloxy)-1-(p-nitrobenzyloxycarbonyl)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: 95.0%

: 108-24-7
acetic anhydride

: 466651-69-4
(4R,2S)-4-(tert-butyldimethylsilanyloxy)-2-[((R)-4-hydroxymethyl)thiazolidin-2-yl]-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

: 466651-70-7
(2S,4R)-2-[((R)-4-acetoxymethyl)thiazolidin-2-yl]-4-(tert-butyldimethylsilanyloxy)-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1002/1521-4184(200204)335:4<152::AID-ARDP152>3.0.CO;2-B

Reference yield:

: 137049-21-9
(2S,4R)-2-formyl-4-tert-butyldimethylsilyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

: 466651-70-7
(2S,4R)-2-[((R)-4-acetoxymethyl)thiazolidin-2-yl]-4-(tert-butyldimethylsilanyloxy)-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

Guidance literature:: Multi-step reaction with 3 steps

1: 77.3 percent / NaHCO₃ / ethanol; H₂O / 24 h / 20 °C

2: 67.3 percent / NaBH₄ / ethanol / 5 h / 0 °C

3: 95 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

With sodium tetrahydroborate; sodium hydrogencarbonate; triethylamine; In ethanol; dichloromethane; water;
DOI:10.1002/1521-4184(200204)335:4<152::AID-ARDP152>3.0.CO;2-B

Reference yield:

: 466651-68-3
(4R,2S)-4-(tert-butyldimethylsilanyloxy)-2-[((R)-4-ethoxycarbonyl)thiazolidin-2-yl]-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

: 466651-70-7
(2S,4R)-2-[((R)-4-acetoxymethyl)thiazolidin-2-yl]-4-(tert-butyldimethylsilanyloxy)-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

Guidance literature:: Multi-step reaction with 2 steps

1: 67.3 percent / NaBH₄ / ethanol / 5 h / 0 °C

2: 95 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

With sodium tetrahydroborate; triethylamine; In ethanol; dichloromethane;
DOI:10.1002/1521-4184(200204)335:4<152::AID-ARDP152>3.0.CO;2-B