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

Base Information

• Chemical Name: 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
• CAS No.: 637767-42-1
• Molecular Formula: C₄₁H₄₃N₃O₇
• Molecular Weight: 689.808

Synonyms: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

Chemical Property of 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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Technology Process of 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

There total 7 articles about 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 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: 82.0%

pent-4-enoic acid (591-80-0) + (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) → 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[5.2.1.01,5]dec-8-ene-6-carbonyl]-amino}-2-phenyl-ethyl ester (637767-42-1)

Guidance literature:

With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane;

DOI:10.1021/ol035773h

Reference yield:

(2S)-2-phenylglycinol (20989-17-7) → 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[5.2.1.01,5]dec-8-ene-6-carbonyl]-amino}-2-phenyl-ethyl ester (637767-42-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / EDC; DMAP; Et₃N / CH₂Cl₂ / 16 h / 20 °C

2: 82 percent / EDC; Et₃N; DMAP / CH₂Cl₂

With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane;

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 → 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[5.2.1.01,5]dec-8-ene-6-carbonyl]-amino}-2-phenyl-ethyl ester (637767-42-1)

Guidance literature:

Multi-step reaction with 6 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

6: 82 percent / EDC; Et₃N; DMAP / CH₂Cl₂

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

upstream raw materials:

pent-4-enoic acid

(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]

(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

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