dibenzyl (2S,4S)-4-(phenylselanyl)pyrrolidine-1,2-dicarboxylate

Base Information

• Chemical Name: dibenzyl (2S,4S)-4-(phenylselanyl)pyrrolidine-1,2-dicarboxylate
• CAS No.: 159551-88-9
• Molecular Formula: C₂₆H₂₅NO₄Se
• Molecular Weight: 494.449
• Mol file: 159551-88-9.mol

Synonyms:dibenzyl (2S,4S)-4-(phenylselanyl)pyrrolidine-1,2-dicarboxylate

Chemical Property of dibenzyl (2S,4S)-4-(phenylselanyl)pyrrolidine-1,2-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of dibenzyl (2S,4S)-4-(phenylselanyl)pyrrolidine-1,2-dicarboxylate

There total 10 articles about dibenzyl (2S,4S)-4-(phenylselanyl)pyrrolidine-1,2-dicarboxylate 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: 79.0%

diphenyl diselenide (1666-13-3) + dibenzyl (2S,4R)-4-((methylsulfonyl)oxy)pyrrolidine-1,2-dicarboxylate → dibenzyl (2S,4S)-4-(phenylselanyl)pyrrolidine-1,2-dicarboxylate (159551-88-9)

Guidance literature:

With sodium tetrahydroborate; In tert-butyl alcohol; at 80 ℃; for 3h;

DOI:10.1021/acs.joc.7b02177

Reference yield: 74.0%

diphenyl diselenide (1666-13-3) + (2S,4R)-Nα-Cbz-4-[(p-toluenesulfonyl)oxy]proline benzyl ester (159551-87-8) → dibenzyl (2S,4S)-4-(phenylselanyl)pyrrolidine-1,2-dicarboxylate (159551-88-9)

Guidance literature:

With sodium tetrahydroborate; In tert-butyl alcohol; Heating;

DOI:10.1016/S0040-4039(00)60753-0

Reference yield:

N-benzyloxycarbonyl-(2S,4R)-4-hydroxyproline benzyl ester (13500-53-3) → dibenzyl (2S,4S)-4-(phenylselanyl)pyrrolidine-1,2-dicarboxylate (159551-88-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / N-methylimidazole / tetrahydrofuran / 0 - 30 °C

2: 74 percent / NaBH₄ / 2-methyl-propan-2-ol / 2.5 h / Heating

With 1-methyl-1H-imidazole; sodium tetrahydroborate; In tetrahydrofuran; tert-butyl alcohol; 1: Tosylation / 2: Substitution;

DOI:10.1016/S0040-4020(97)10352-0

upstream raw materials:

diphenyl diselenide

(2S,4R)-N^α-Cbz-4-[(p-toluenesulfonyl)oxy]proline benzyl ester

N-benzyloxycarbonyl-(2S,4R)-4-hydroxyproline benzyl ester

benzyl chloroformate

Downstream raw materials:

dibenzyl (2S,3R,4S)-3,4-dihydroxypyrrolidine-1,2-dicarboxylate

(2S,3RS,4SR)-N-benzyloxycarbonyl-3,4-dihydroxyproline benzyl ester

(2S,3R,4R)-N-benzyloxycarbonyl-3-azido-4-hydroxyproline benzyl ester

(2S,3R,4R)-N-benzyloxycarbonyl-3-hydroxy-4-azidoproline benzyl ester