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

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Chemical Name:(2S,4R)-2-[((R)-4-acetoxymethyl)thiazolidin-2-yl]-4-methanesulfonyloxy-1-(p-nitrobenzyloxycarbonyl)pyrrolidine
CAS No.:466651-71-8
Molecular Formula:C₁₉H₂₅N₃O₉S₂
Molecular Weight:503.554
Hs Code.:

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

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

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

There total 4 articles about (2S,4R)-2-[((R)-4-acetoxymethyl)thiazolidin-2-yl]-4-methanesulfonyloxy-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: 69.0%

: 124-63-0
methanesulfonyl chloride

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

: 466651-71-8
(2S,4R)-2-[((R)-4-acetoxymethyl)thiazolidin-2-yl]-4-methanesulfonyloxy-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

Guidance literature:: (2S,4R)-2-[((R)-4-acetoxymethyl)thiazolidin-2-yl]-4-(tert-butyldimethylsilanyloxy)-1-(p-nitrobenzyloxycarbonyl)pyrrolidine; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;

methanesulfonyl chloride; 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

: 466651-71-8
(2S,4R)-2-[((R)-4-acetoxymethyl)thiazolidin-2-yl]-4-methanesulfonyloxy-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1.1: 77.3 percent / NaHCO₃ / ethanol; H₂O / 24 h / 20 °C

2.1: 67.3 percent / NaBH₄ / ethanol / 5 h / 0 °C

3.1: 95 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

4.1: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

4.2: 69 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

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

Reference yield:

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

: 466651-71-8
(2S,4R)-2-[((R)-4-acetoxymethyl)thiazolidin-2-yl]-4-methanesulfonyloxy-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

Guidance literature:: Multi-step reaction with 2 steps

1.1: 95 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

2.1: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

2.2: 69 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

With tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1002/1521-4184(200204)335:4<152::AID-ARDP152>3.0.CO;2-B