(2S,4S,5R)-4-(benzoyloxy)-5-acetoxy-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(2-(trimethylsilyl)ethyl) diester

Base Information

Chemical Name:(2S,4S,5R)-4-(benzoyloxy)-5-acetoxy-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(2-(trimethylsilyl)ethyl) diester
CAS No.:132592-22-4
Molecular Formula:C₂₁H₂₉NO₈Si
Molecular Weight:451.549
Hs Code.:

Synonyms:(2S,4S,5R)-4-(benzoyloxy)-5-acetoxy-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(2-(trimethylsilyl)ethyl) diester

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Chemical Property of (2S,4S,5R)-4-(benzoyloxy)-5-acetoxy-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(2-(trimethylsilyl)ethyl) diester

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Technology Process of (2S,4S,5R)-4-(benzoyloxy)-5-acetoxy-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(2-(trimethylsilyl)ethyl) diester

There total 4 articles about (2S,4S,5R)-4-(benzoyloxy)-5-acetoxy-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(2-(trimethylsilyl)ethyl) diester 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: 34.0%

: 108-24-7
acetic anhydride

: 132592-20-2,132592-21-3
(2S,4S,5RS)-4-(benzoyloxy)-5-methoxy-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(2-(trimethylsilyl)ethyl) diester

: 132592-22-4
(2S,4S,5R)-4-(benzoyloxy)-5-acetoxy-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(2-(trimethylsilyl)ethyl) diester

Guidance literature:: With sulfuric acid; In dichloromethane; acetic acid; at 0 ℃; for 3h;
DOI:10.1021/jo00008a040

Reference yield:

: 128359-95-5
(2S,4S)-Methyl 4-acetoxy-1-<<2-(trimethylsilyl)ethyl>oxycarbonyl>pyrrolidine-2-carboxylate

: 132592-22-4
(2S,4S,5R)-4-(benzoyloxy)-5-acetoxy-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(2-(trimethylsilyl)ethyl) diester

Guidance literature:: Multi-step reaction with 4 steps

1: 66 percent / Ambient temperature; electrolysis (0.5 A); other proline derivatives; dependence of yiled from protection groups

2: 2.4 g / NaOMe / methanol / 0.5 h / Ambient temperature

3: 68 percent / DMAP / CH₂Cl₂ / 2 h / 10 - 15 °C

4: 34 percent / conc. H₂SO₄ / acetic acid; CH₂Cl₂ / 3 h / 0 °C

With dmap; sulfuric acid; sodium methylate; In methanol; dichloromethane; acetic acid;
DOI:10.1021/jo00008a040

Reference yield:

: 129001-50-9,129001-52-1
(2S,4S,5RS)-4-acetoxy-5-methoxy-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(2-(trimethylsilyl)ethyl) diester

: 132592-22-4
(2S,4S,5R)-4-(benzoyloxy)-5-acetoxy-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(2-(trimethylsilyl)ethyl) diester

Guidance literature:: Multi-step reaction with 3 steps

1: 2.4 g / NaOMe / methanol / 0.5 h / Ambient temperature

2: 68 percent / DMAP / CH₂Cl₂ / 2 h / 10 - 15 °C

3: 34 percent / conc. H₂SO₄ / acetic acid; CH₂Cl₂ / 3 h / 0 °C

With dmap; sulfuric acid; sodium methylate; In methanol; dichloromethane; acetic acid;
DOI:10.1021/jo00008a040