ethyl (R,E)-4-((tert-butoxycarbonyl)(hydroxy)amino)-5-phenylpent-2-enoate

Base Information

• Chemical Name: ethyl (R,E)-4-((tert-butoxycarbonyl)(hydroxy)amino)-5-phenylpent-2-enoate
• CAS No.: 1569092-93-8
• Molecular Formula: C₁₈H₂₅NO₅
• Molecular Weight: 335.4

Synonyms:ethyl (R,E)-4-((tert-butoxycarbonyl)(hydroxy)amino)-5-phenylpent-2-enoate

Chemical Property of ethyl (R,E)-4-((tert-butoxycarbonyl)(hydroxy)amino)-5-phenylpent-2-enoate

Chemical Property:

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Technology Process of ethyl (R,E)-4-((tert-butoxycarbonyl)(hydroxy)amino)-5-phenylpent-2-enoate

There total 2 articles about ethyl (R,E)-4-((tert-butoxycarbonyl)(hydroxy)amino)-5-phenylpent-2-enoate 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:

3-phenyl-propionaldehyde (104-53-0) → ethyl (R,E)-4-((tert-butoxycarbonyl)(hydroxy)amino)-5-phenylpent-2-enoate (1569092-93-8) + ethyl (R,Z)-4-((tert-butoxycarbonyl)(hydroxy)amino)-5-phenylpent-2-enoate (1569092-98-3)

Guidance literature:

Multi-step reaction with 2 steps

1: (2R)-2-tritylpyrrolidine; manganese(IV) oxide / dichloromethane / 20 h / 0 °C

2: dichloromethane / 20 °C

With manganese(IV) oxide; (2R)-2-tritylpyrrolidine; In dichloromethane; 2: |Wittig Olefination;

DOI:10.1021/ol5000742

Reference yield:

tert-Butyl N-hydroxycarbamate (36016-38-3) → ethyl (R,E)-4-((tert-butoxycarbonyl)(hydroxy)amino)-5-phenylpent-2-enoate (1569092-93-8) + ethyl (R,Z)-4-((tert-butoxycarbonyl)(hydroxy)amino)-5-phenylpent-2-enoate (1569092-98-3)

Guidance literature:

Multi-step reaction with 2 steps

1: (2R)-2-tritylpyrrolidine; manganese(IV) oxide / dichloromethane / 20 h / 0 °C

2: dichloromethane / 20 °C

With manganese(IV) oxide; (2R)-2-tritylpyrrolidine; In dichloromethane; 2: |Wittig Olefination;

DOI:10.1021/ol5000742

Reference yield: 68.0%

ethyl (R,E)-4-((tert-butoxycarbonyl)(hydroxy)amino)-5-phenylpent-2-enoate (1569092-93-8) → ethyl (S)-4-((tert-butoxycarbonyl)amino)-5-phenylpentanoate (790223-53-9)

Guidance literature:

With palladium on activated charcoal; hydrogen; acetic acid; at 60 ℃; for 48h;

DOI:10.1021/ol5000742

upstream raw materials:

3-phenyl-propionaldehyde

tert-Butyl N-hydroxycarbamate

Downstream raw materials:

ethyl (R,E)-4-((tert-butoxycarbonyl)amino)-5-phenylpent-2-enoate

ethyl (R,Z)-4-((tert-butoxycarbonyl)amino)-5-phenylpent-2-enoate

ethyl (S)-4-((tert-butoxycarbonyl)amino)-5-phenylpentanoate

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