(1R,2R,5S,6S,7S)-3-(4-Methoxy-benzyl)-4-oxo-10-oxa-3-aza-tricyclo[5.2.1.0^1,5]dec-8-ene-2,6-dicarboxylic acid 2-(allyl-benzyl-amide) 6-[((S)-2-hydroxy-1-phenyl-ethyl)-amide]

Base Information

• Chemical Name: (1R,2R,5S,6S,7S)-3-(4-Methoxy-benzyl)-4-oxo-10-oxa-3-aza-tricyclo[5.2.1.0^1,5]dec-8-ene-2,6-dicarboxylic acid 2-(allyl-benzyl-amide) 6-[((S)-2-hydroxy-1-phenyl-ethyl)-amide]
• CAS No.: 637767-56-7
• Molecular Formula: C₃₆H₃₇N₃O₆
• Molecular Weight: 607.706

Synonyms:(1R,2R,5S,6S,7S)-3-(4-Methoxy-benzyl)-4-oxo-10-oxa-3-aza-tricyclo[5.2.1.0^1,5]dec-8-ene-2,6-dicarboxylic acid 2-(allyl-benzyl-amide) 6-[((S)-2-hydroxy-1-phenyl-ethyl)-amide]

Chemical Property of (1R,2R,5S,6S,7S)-3-(4-Methoxy-benzyl)-4-oxo-10-oxa-3-aza-tricyclo[5.2.1.0^1,5]dec-8-ene-2,6-dicarboxylic acid 2-(allyl-benzyl-amide) 6-[((S)-2-hydroxy-1-phenyl-ethyl)-amide]

Chemical Property:

Purity/Quality:

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Technology Process of (1R,2R,5S,6S,7S)-3-(4-Methoxy-benzyl)-4-oxo-10-oxa-3-aza-tricyclo[5.2.1.0^1,5]dec-8-ene-2,6-dicarboxylic acid 2-(allyl-benzyl-amide) 6-[((S)-2-hydroxy-1-phenyl-ethyl)-amide]

There total 5 articles about (1R,2R,5S,6S,7S)-3-(4-Methoxy-benzyl)-4-oxo-10-oxa-3-aza-tricyclo[5.2.1.0^1,5]dec-8-ene-2,6-dicarboxylic acid 2-(allyl-benzyl-amide) 6-[((S)-2-hydroxy-1-phenyl-ethyl)-amide] 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%

(2S)-2-phenylglycinol (20989-17-7) + (1R,2R,5S,6S,7S)-2-(Allyl-benzyl-carbamoyl)-3-(4-methoxy-benzyl)-4-oxo-10-oxa-3-aza-tricyclo[5.2.1.01,5]dec-8-ene-6-carboxylic acid (637767-44-3) → (1R,2R,5S,6S,7S)-3-(4-Methoxy-benzyl)-4-oxo-10-oxa-3-aza-tricyclo[5.2.1.01,5]dec-8-ene-2,6-dicarboxylic acid 2-(allyl-benzyl-amide) 6-[((S)-2-hydroxy-1-phenyl-ethyl)-amide] (637767-56-7)

Guidance literature:

With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/ol035773h

Reference yield:

(1S,2S,5R,6R,7R)-2-Benzylcarbamoyl-3-(4-methoxy-benzyl)-4-oxo-10-oxa-3-aza-tricyclo[5.2.1.01,5]dec-8-ene-6-carboxylic acid ethyl ester → (1R,2R,5S,6S,7S)-3-(4-Methoxy-benzyl)-4-oxo-10-oxa-3-aza-tricyclo[5.2.1.01,5]dec-8-ene-2,6-dicarboxylic acid 2-(allyl-benzyl-amide) 6-[((S)-2-hydroxy-1-phenyl-ethyl)-amide] (637767-56-7)

Guidance literature:

Multi-step reaction with 5 steps

1: CsOH*H₂O / tetrahydrofuran / 8 h / 20 °C

2: Ba(OH)2*8H₂O / tetrahydrofuran / 12 h / 20 °C

3: 45 percent / EDC*HCl; DMAP / CH₂Cl₂ / 20 °C

4: 93 percent / Ba(OH)2*8H₂O / methanol / 12 h / 20 °C

5: 68 percent / EDC; DMAP; Et₃N / CH₂Cl₂ / 16 h / 20 °C

With dmap; barium dihydroxide; cesium hydroxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ol035773h

Reference yield:

(1S,2S,5R,6R,7R)-2-(Allyl-benzyl-carbamoyl)-3-(4-methoxy-benzyl)-4-oxo-10-oxa-3-aza-tricyclo[5.2.1.01,5]dec-8-ene-6-carboxylic acid → (1R,2R,5S,6S,7S)-3-(4-Methoxy-benzyl)-4-oxo-10-oxa-3-aza-tricyclo[5.2.1.01,5]dec-8-ene-2,6-dicarboxylic acid 2-(allyl-benzyl-amide) 6-[((S)-2-hydroxy-1-phenyl-ethyl)-amide] (637767-56-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 45 percent / EDC*HCl; DMAP / CH₂Cl₂ / 20 °C

2: 93 percent / Ba(OH)2*8H₂O / methanol / 12 h / 20 °C

3: 68 percent / EDC; DMAP; Et₃N / CH₂Cl₂ / 16 h / 20 °C

With dmap; barium dihydroxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In methanol; dichloromethane;

DOI:10.1021/ol035773h

upstream raw materials:

(2S)-2-phenylglycinol

(1R,2R,5S,6S,7S)-2-(Allyl-benzyl-carbamoyl)-3-(4-methoxy-benzyl)-4-oxo-10-oxa-3-aza-tricyclo[5.2.1.0^1,5]dec-8-ene-6-carboxylic acid

(1R,2R,5S,6S,7S)-2-(Allyl-benzyl-carbamoyl)-3-(4-methoxy-benzyl)-4-oxo-10-oxa-3-aza-tricyclo[5.2.1.0^1,5]dec-8-ene-6-carboxylic acid (1R,2R)-2-(methyl-pent-4-enoyl-amino)-1-phenyl-propyl ester

Downstream raw materials:

Pent-4-enoic acid (S)-2-{[(1R,2R,5S,6S,7S)-2-(allyl-benzyl-carbamoyl)-3-(4-methoxy-benzyl)-4-oxo-10-oxa-3-aza-tricyclo[5.2.1.0^1,5]dec-8-ene-6-carbonyl]-amino}-2-phenyl-ethyl ester

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