(3S,8aS)-5-Oxo-3-phenylselanylmethyl-hexahydro-indolizine-8a-carboxylic acid ethyl ester

Base Information

• Chemical Name: (3S,8aS)-5-Oxo-3-phenylselanylmethyl-hexahydro-indolizine-8a-carboxylic acid ethyl ester
• CAS No.: 754983-60-3
• Molecular Formula: C₁₈H₂₃NO₃Se
• Molecular Weight: 380.346
• Mol file: 754983-60-3.mol

Synonyms:(3S,8aS)-5-Oxo-3-phenylselanylmethyl-hexahydro-indolizine-8a-carboxylic acid ethyl ester

Chemical Property of (3S,8aS)-5-Oxo-3-phenylselanylmethyl-hexahydro-indolizine-8a-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,8aS)-5-Oxo-3-phenylselanylmethyl-hexahydro-indolizine-8a-carboxylic acid ethyl ester

There total 1 articles about (3S,8aS)-5-Oxo-3-phenylselanylmethyl-hexahydro-indolizine-8a-carboxylic acid ethyl 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: 68.0%

Phenylselenyl bromide (34837-55-3) + (S)-2-But-3-enyl-6-oxo-piperidine-2-carboxylic acid ethyl ester (180787-81-9) → (3S,8aS)-5-Oxo-3-phenylselanylmethyl-hexahydro-indolizine-8a-carboxylic acid ethyl ester (754983-60-3) + (3R,8aS)-5-Oxo-3-phenylselanylmethyl-hexahydro-indolizine-8a-carboxylic acid ethyl ester

Guidance literature:

With silica gel; In acetonitrile; at 20 ℃;

DOI:10.1016/j.tetlet.2004.06.051

Reference yield:

(3S,8aS)-5-Oxo-3-phenylselanylmethyl-hexahydro-indolizine-8a-carboxylic acid ethyl ester (754983-60-3) → (3S,6S,8aS)-6-Amino-3-((S)-1-carboxy-2-phenyl-ethylcarbamoyl)-5-oxo-hexahydro-indolizine-8a-carboxylic acid ethyl ester

Guidance literature:

Multi-step reaction with 7 steps

1.1: m-chloro perbenzoic acid (mCPBA); KOH / tetrahydrofuran / 8 h / Heating

1.2: 82 percent / tetrahydrofuran / 12 h / 20 °C

2.1: 86 percent / NaH

3.1: 72 percent / lithium hexamethylsiliazide (LHMDS)

4.1: H₂ / Pd/C

5.1: NaIO₄; RuCl₃

6.1: CF₃COOH

6.2: H₂ / Pd/C

With ruthenium trichloride; potassium hydroxide; sodium periodate; hydrogen; sodium hydride; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1016/j.tetlet.2004.06.051

Reference yield:

(3S,8aS)-5-Oxo-3-phenylselanylmethyl-hexahydro-indolizine-8a-carboxylic acid ethyl ester (754983-60-3) → (3S,6S,8aS)-6-((S)-2-Amino-3-phenyl-propionylamino)-3-((S)-1-carboxy-2-phenyl-ethylcarbamoyl)-5-oxo-hexahydro-indolizine-8a-carboxylic acid ethyl ester

Guidance literature:

Multi-step reaction with 8 steps

1.1: m-chloro perbenzoic acid (mCPBA); KOH / tetrahydrofuran / 8 h / Heating

1.2: 82 percent / tetrahydrofuran / 12 h / 20 °C

2.1: 86 percent / NaH

3.1: 72 percent / lithium hexamethylsiliazide (LHMDS)

4.1: H₂ / Pd/C

5.1: NaIO₄; RuCl₃

6.1: CF₃COOH

6.2: H₂ / Pd/C

With ruthenium trichloride; potassium hydroxide; sodium periodate; hydrogen; sodium hydride; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1016/j.tetlet.2004.06.051

upstream raw materials:

Phenylselenyl bromide

(S)-2-But-3-enyl-6-oxo-piperidine-2-carboxylic acid ethyl ester

Downstream raw materials:

(3S,8aS)-3-Benzyloxymethyl-5-oxo-hexahydro-indolizine-8a-carboxylic acid ethyl ester

C₂₉H₄₃N₃O₈

C₃₁H₄₄N₄O₁₀