(1R,5S,7R)-1,5,7-Tris-benzyloxymethyl-2,4-dioxo-3-aza-bicyclo[3.3.1]nonane-7-carboxylic acid biphenyl-4-ylamide

Base Information

• Chemical Name: (1R,5S,7R)-1,5,7-Tris-benzyloxymethyl-2,4-dioxo-3-aza-bicyclo[3.3.1]nonane-7-carboxylic acid biphenyl-4-ylamide
• CAS No.: 146651-55-0
• Molecular Formula: C₄₅H₄₄N₂O₆
• Molecular Weight: 708.854

Synonyms:(1R,5S,7R)-1,5,7-Tris-benzyloxymethyl-2,4-dioxo-3-aza-bicyclo[3.3.1]nonane-7-carboxylic acid biphenyl-4-ylamide

Chemical Property of (1R,5S,7R)-1,5,7-Tris-benzyloxymethyl-2,4-dioxo-3-aza-bicyclo[3.3.1]nonane-7-carboxylic acid biphenyl-4-ylamide

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

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Technology Process of (1R,5S,7R)-1,5,7-Tris-benzyloxymethyl-2,4-dioxo-3-aza-bicyclo[3.3.1]nonane-7-carboxylic acid biphenyl-4-ylamide

There total 7 articles about (1R,5S,7R)-1,5,7-Tris-benzyloxymethyl-2,4-dioxo-3-aza-bicyclo[3.3.1]nonane-7-carboxylic acid biphenyl-4-ylamide 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:

benzyl bromomethyl ether (17690-16-3) → (1R,5S,7R)-1,5,7-Tris-benzyloxymethyl-2,4-dioxo-3-aza-bicyclo[3.3.1]nonane-7-carboxylic acid biphenyl-4-ylamide (146651-55-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) LDA

2: KOH / ethanol / Heating

3: xylene / Heating

4: aq. NH₃

5: SOCl₂

6: pyridine

With pyridine; potassium hydroxide; ammonium hydroxide; thionyl chloride; lithium diisopropyl amide; In ethanol; xylene;

DOI:10.1021/ja00055a066

Reference yield:

trimethyl cyclohexane-1,3,5-tricarboxylate (52831-11-5) → (1R,5S,7R)-1,5,7-Tris-benzyloxymethyl-2,4-dioxo-3-aza-bicyclo[3.3.1]nonane-7-carboxylic acid biphenyl-4-ylamide (146651-55-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) LDA

2: KOH / ethanol / Heating

3: xylene / Heating

4: aq. NH₃

5: SOCl₂

6: pyridine

With pyridine; potassium hydroxide; ammonium hydroxide; thionyl chloride; lithium diisopropyl amide; In ethanol; xylene;

DOI:10.1021/ja00055a066

Reference yield:

1,3,5-Tris-benzyloxymethyl-cyclohexane-1,3,5-tricarboxylic acid trimethyl ester (146651-50-5) → (1R,5S,7R)-1,5,7-Tris-benzyloxymethyl-2,4-dioxo-3-aza-bicyclo[3.3.1]nonane-7-carboxylic acid biphenyl-4-ylamide (146651-55-0)

Guidance literature:

Multi-step reaction with 5 steps

1: KOH / ethanol / Heating

2: xylene / Heating

3: aq. NH₃

4: SOCl₂

5: pyridine

With pyridine; potassium hydroxide; ammonium hydroxide; thionyl chloride; In ethanol; xylene;

DOI:10.1021/ja00055a066

upstream raw materials:

4-phenylalanine

(1S,5R,7S)-1,5,7-Tris-benzyloxymethyl-2,4-dioxo-3-aza-bicyclo[3.3.1]nonane-7-carbonyl chloride

benzyl bromomethyl ether

trimethyl cyclohexane-1,3,5-tricarboxylate

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