(2S,3S,4S)-4-Benzyl-3-tert-butoxycarbonylmethyl-4-ethoxycarbonyl-2-hydroxymethyl-5-oxopyrrolidine

Base Information

• Chemical Name: (2S,3S,4S)-4-Benzyl-3-tert-butoxycarbonylmethyl-4-ethoxycarbonyl-2-hydroxymethyl-5-oxopyrrolidine
• CAS No.: 204929-80-6
• Molecular Formula: C₂₁H₂₉NO₆
• Molecular Weight: 391.464

Synonyms:(2S,3S,4S)-4-Benzyl-3-tert-butoxycarbonylmethyl-4-ethoxycarbonyl-2-hydroxymethyl-5-oxopyrrolidine

Chemical Property of (2S,3S,4S)-4-Benzyl-3-tert-butoxycarbonylmethyl-4-ethoxycarbonyl-2-hydroxymethyl-5-oxopyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S)-4-Benzyl-3-tert-butoxycarbonylmethyl-4-ethoxycarbonyl-2-hydroxymethyl-5-oxopyrrolidine

There total 4 articles about (2S,3S,4S)-4-Benzyl-3-tert-butoxycarbonylmethyl-4-ethoxycarbonyl-2-hydroxymethyl-5-oxopyrrolidine 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:

(2R,5S,6S)-7-Ethoxycarbonyl-6-tert-butoxycarbonylmethyl-8-oxo-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octane (204929-66-8) → (2S,3S,4S)-4-Benzyl-3-tert-butoxycarbonylmethyl-4-ethoxycarbonyl-2-hydroxymethyl-5-oxopyrrolidine (204929-80-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / tetrahydrofuran / 0 °C

1.2: 34 percent / tetrahydrofuran / 14 h / Heating

2.1: 86 percent / TFA / CH₂Cl₂ / 1 h / 20 °C

With sodium hydride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; 1.1: Metallation / 1.2: Alkylation / 2.1: Ring cleavage;

DOI:10.1039/b002001j

Reference yield:

bromoacetic acid tert-butyl ester (5292-43-3) → (2S,3S,4S)-4-Benzyl-3-tert-butoxycarbonylmethyl-4-ethoxycarbonyl-2-hydroxymethyl-5-oxopyrrolidine (204929-80-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / DMPU / tetrahydrofuran

2: NaH / tetrahydrofuran / Heating

3: TFA / CH₂Cl₂

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1039/a708429c

Reference yield:

(2R,5S)-7-ethoxycarbonyl-8-oxo-2-phenyl-1-aza-3-oxa-bicyclo[3.3.0]oct-6-ene (166765-36-2) → (2S,3S,4S)-4-Benzyl-3-tert-butoxycarbonylmethyl-4-ethoxycarbonyl-2-hydroxymethyl-5-oxopyrrolidine (204929-80-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / DMPU / tetrahydrofuran

2: NaH / tetrahydrofuran / Heating

3: TFA / CH₂Cl₂

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1039/a708429c

upstream raw materials:

benzyl bromide

(2R,5S,6S)-7-Ethoxycarbonyl-6-tert-butoxycarbonylmethyl-8-oxo-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octane

bromoacetic acid tert-butyl ester

(2R,5S)-7-ethoxycarbonyl-8-oxo-2-phenyl-1-aza-3-oxa-bicyclo[3.3.0]oct-6-ene

Downstream raw materials:

(2S,3S,4S)-4-Benzyl-3-tert-butoxycarbonylmethyl-4-carboxy-2-hydroxymethyl-5-oxopyrrolidine

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