(1S,2S,5R,6R,7R)-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

Base Information

• Chemical Name: (1S,2S,5R,6R,7R)-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
• CAS No.: 637767-23-8
• Molecular Formula: C₄₃H₄₇N₃O₇
• Molecular Weight: 717.862

Synonyms:(1S,2S,5R,6R,7R)-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

Chemical Property of (1S,2S,5R,6R,7R)-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

Chemical Property:

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Technology Process of (1S,2S,5R,6R,7R)-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

There total 5 articles about (1S,2S,5R,6R,7R)-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 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: 47.0%

pent-4-enoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenylethyl)-methylamide (637767-50-1) + (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 → (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)-2-(methyl-pent-4-enoyl-amino)-1-phenyl-propyl ester (637767-23-8) + (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 (1R,2R)-2-(methyl-pent-4-enoyl-amino)-1-phenyl-propyl ester (637767-24-9)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃;

DOI:10.1021/ol035773h

Reference yield:

pent-4-enoic acid (591-80-0) → (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)-2-(methyl-pent-4-enoyl-amino)-1-phenyl-propyl ester (637767-23-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / Et₃N; EDC; DMAP / CH₂Cl₂ / 12 h / 20 °C

2: 47 percent / EDC*HCl; DMAP / CH₂Cl₂ / 20 °C

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

DOI:10.1021/ol035773h

Reference yield:

(1R,2R)-pseudoephedrine (321-97-1,7009-81-6,90-83-5,6912-63-6) → (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)-2-(methyl-pent-4-enoyl-amino)-1-phenyl-propyl ester (637767-23-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / Et₃N; EDC; DMAP / CH₂Cl₂ / 12 h / 20 °C

2: 47 percent / EDC*HCl; DMAP / CH₂Cl₂ / 20 °C

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

DOI:10.1021/ol035773h

upstream raw materials:

pent-4-enoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenylethyl)-methylamide

pent-4-enoic acid

(1R,2R)-pseudoephedrine

Downstream raw materials:

(1S,2S,5R,6R,7R)-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 (1S,2S)-3-methoxy-2-pent-4-enoylamino-1-phenyl-propyl ester

(1S,2S,5R,6R,7R)-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 (1S,2R)-2-pent-4-enoylamino-1-phenyl-propyl ester

(1S,2S,5R,6R,7R)-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 (S)-2-pent-4-enoylamino-1-phenyl-ethyl ester

Pent-4-enoic acid (S)-2-{[(1S,2S,5R,6R,7R)-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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