(5R,4S,2S)-4-hydroxy-5-((phenylmethoxy)methyl)-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester

Base Information

Chemical Name:(5R,4S,2S)-4-hydroxy-5-((phenylmethoxy)methyl)-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester
CAS No.:132592-32-6
Molecular Formula:C₂₂H₂₅NO₆
Molecular Weight:399.444
Hs Code.:

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

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

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

There total 15 articles about (5R,4S,2S)-4-hydroxy-5-((phenylmethoxy)methyl)-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: 100.0%

: 128359-94-4
(5R,4S,2S)-4-acetoxy-5-((phenylmethoxy)methyl)-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester

: 132592-32-6
(5R,4S,2S)-4-hydroxy-5-((phenylmethoxy)methyl)-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester

Guidance literature:: With sodium methylate; In methanol; for 1h; Ambient temperature;
DOI:10.1021/jo00008a040

Reference yield: 46.0%

: C₂₃H₂₇NO₆

: 18107-18-1
diazomethyl-trimethyl-silane

: 132592-32-6
(5R,4S,2S)-4-hydroxy-5-((phenylmethoxy)methyl)-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester

Guidance literature:: C₂₃H₂₇NO₆; With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 1.5h;

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tetrahydrofuran; water; tert-butyl alcohol; for 1h;

diazomethyl-trimethyl-silane; Further stages;
DOI:10.1021/acsinfecdis.8b00105

Reference yield:

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

: 132592-32-6
(5R,4S,2S)-4-hydroxy-5-((phenylmethoxy)methyl)-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester

Guidance literature:: Multi-step reaction with 9 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

8: 91 percent / Ag₂O / CH₂Cl₂ / Heating; a) 10h, b) 12h

9: 100 percent / NaOMe / methanol / 1 h / Ambient temperature

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