(2S,3S)-2-[(E)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-vinyl]-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2S,3S)-2-[(E)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-vinyl]-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester
• CAS No.: 211570-38-6
• Molecular Formula: C₁₉H₂₅NO₅
• Molecular Weight: 347.411

Synonyms:(2S,3S)-2-[(E)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-vinyl]-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property of (2S,3S)-2-[(E)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-vinyl]-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (2S,3S)-2-[(E)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-vinyl]-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

There total 9 articles about (2S,3S)-2-[(E)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-vinyl]-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester 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: 90.0%

sodium phenyl-methanolate (20194-18-7) + 2,2,2-Trichloro-1-{(2S,3S)-2-[(E)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-vinyl]-3-hydroxy-pyrrolidin-1-yl}-ethanone (211570-37-5) → (2S,3S)-2-[(E)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-vinyl]-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester (211570-38-6)

Guidance literature:

In tetrahydrofuran; at 20 ℃;

DOI:10.1039/a802741b

Reference yield:

(S)-3,4-O-isopropylidene-3,4-dihydroxybutyltriphenylphosphonium iodide (114884-40-1) → (2S,3S)-2-[(E)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-vinyl]-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester (211570-38-6)

Guidance literature:

Multi-step reaction with 9 steps

2: 86 percent / PPTS / methanol / 0 °C

3: 92 percent / imidazole / dimethylformamide; CH₂Cl₂ / -60 °C

4: DBU / acetonitrile / 0 °C

5: 1.) methyl 2,2,2-trichloroacetimidate, Et₃N, 2.) PPTS / 1.) MeCN, -20 to -15 deg C, 2.) MeOH, H₂O, 20 deg C

6: 84 percent / H₂O₂ / H₂O; tetrahydrofuran / 0 - 20 °C

7: 92 percent / Bu₄NF / tetrahydrofuran / -5 - 0 °C

8: 88 percent / DIAD, PPh₃ / tetrahydrofuran / 0 °C

9: 90 percent / tetrahydrofuran / 20 °C

With 1H-imidazole; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; dihydrogen peroxide; pyridinium p-toluenesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; methyl 2,2,2-trichloroacetimidate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/a802741b

Reference yield:

(Z)-(S)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hex-4-ene-1,3-diol (211518-41-1) → (2S,3S)-2-[(E)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-vinyl]-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester (211570-38-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 92 percent / imidazole / dimethylformamide; CH₂Cl₂ / -60 °C

2: DBU / acetonitrile / 0 °C

3: 1.) methyl 2,2,2-trichloroacetimidate, Et₃N, 2.) PPTS / 1.) MeCN, -20 to -15 deg C, 2.) MeOH, H₂O, 20 deg C

4: 84 percent / H₂O₂ / H₂O; tetrahydrofuran / 0 - 20 °C

5: 92 percent / Bu₄NF / tetrahydrofuran / -5 - 0 °C

6: 88 percent / DIAD, PPh₃ / tetrahydrofuran / 0 °C

7: 90 percent / tetrahydrofuran / 20 °C

With 1H-imidazole; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; dihydrogen peroxide; pyridinium p-toluenesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; methyl 2,2,2-trichloroacetimidate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/a802741b

upstream raw materials:

sodium phenyl-methanolate

2,2,2-Trichloro-1-{(2S,3S)-2-[(E)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-vinyl]-3-hydroxy-pyrrolidin-1-yl}-ethanone

(S)-3,4-O-isopropylidene-3,4-dihydroxybutyltriphenylphosphonium iodide

(Z)-(S)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hex-4-ene-1,3-diol

Downstream raw materials:

(2S,3S)-2-[(1R,2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-1,2,3-trihydroxy-butyl]-3-methoxymethoxy-pyrrolidine-1-carboxylic acid benzyl ester

(2R,3S)-2-{(4R,5R)-5-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-3-methoxymethoxy-pyrrolidine-1-carboxylic acid benzyl ester

(2R,3S)-3-Hydroxy-2-[(1R,2S,3R)-1,2,3-trihydroxy-4-(2,4,6-triisopropyl-benzenesulfonyloxy)-butyl]-pyrrolidine-1-carboxylic acid benzyl ester

(2S,3S)-2-[(E)-(S)-4-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-but-1-enyl]-3-methoxymethoxy-pyrrolidine-1-carboxylic acid benzyl ester

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