(5R,4S,2S)-4-acetoxy-5-(hydroxymethyl)-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester

Base Information

Chemical Name:(5R,4S,2S)-4-acetoxy-5-(hydroxymethyl)-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester
CAS No.:132592-31-5
Molecular Formula:C₁₇H₂₁NO₇
Molecular Weight:351.356
Hs Code.:

Synonyms:(5R,4S,2S)-4-acetoxy-5-(hydroxymethyl)-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester

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Chemical Property of (5R,4S,2S)-4-acetoxy-5-(hydroxymethyl)-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester

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Technology Process of (5R,4S,2S)-4-acetoxy-5-(hydroxymethyl)-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester

There total 13 articles about (5R,4S,2S)-4-acetoxy-5-(hydroxymethyl)-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) 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: 93.0%

: C₂₃H₃₅NO₇Si

: 132592-31-5
(5R,4S,2S)-4-acetoxy-5-(hydroxymethyl)-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran;
DOI:10.1021/acsinfecdis.8b00105

Reference yield:

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

: 132592-31-5
(5R,4S,2S)-4-acetoxy-5-(hydroxymethyl)-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester

Guidance literature:: Multi-step reaction with 7 steps

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

2: 86 percent / conc. H₂SO₄ / acetic acid; CH₂Cl₂ / 2 h / 0 °C

3: 72 percent / camphorsulfonic acid / CH₂Cl₂ / 3 h / Ambient temperature

4: 67 percent / Bu₆Sn₂ / benzene / 4 h / Irradiation

5: CH₂Cl₂ / a) 0 deg C, 5 min, b) r.t., 3.5h

6: 10percent aq.NaHCO₃ / CH₂Cl₂ / Ambient temperature

7: 1) O₃, 2) NaBH₄ / 1) MeOH, CH₂Cl₂, -78 deg C, 2) a) to 0 deg C, b) 0 deg C, 45 min

With sodium tetrahydroborate; sulfuric acid; camphor-10-sulfonic acid; bis(tri-n-butyltin); sodium hydrogencarbonate; ozone; In dichloromethane; acetic acid; benzene;
DOI:10.1021/jo00008a040

Reference yield:

: 129001-59-8,129001-61-2
(2S,4S,5RS)-4,5-diacetoxy-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(2-(trimethylsilyl)ethyl) diester

: 132592-31-5
(5R,4S,2S)-4-acetoxy-5-(hydroxymethyl)-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester

Guidance literature:: Multi-step reaction with 5 steps

1: 72 percent / camphorsulfonic acid / CH₂Cl₂ / 3 h / Ambient temperature

2: 67 percent / Bu₆Sn₂ / benzene / 4 h / Irradiation

3: CH₂Cl₂ / a) 0 deg C, 5 min, b) r.t., 3.5h

4: 10percent aq.NaHCO₃ / CH₂Cl₂ / Ambient temperature

5: 1) O₃, 2) NaBH₄ / 1) MeOH, CH₂Cl₂, -78 deg C, 2) a) to 0 deg C, b) 0 deg C, 45 min

With sodium tetrahydroborate; camphor-10-sulfonic acid; bis(tri-n-butyltin); sodium hydrogencarbonate; ozone; In dichloromethane; benzene;
DOI:10.1021/jo00008a040