(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

Base Information

• Chemical Name: (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
• CAS No.: 637767-44-3
• Molecular Formula: C₂₈H₂₈N₂O₆
• Molecular Weight: 488.54

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Technology Process of (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

There total 4 articles about (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 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: 93.0%

(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) → (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)

Guidance literature:

With barium dihydroxide; In methanol; at 20 ℃; for 12h;

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)-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)

Guidance literature:

Multi-step reaction with 4 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

With dmap; barium dihydroxide; cesium hydroxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 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)-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)

Guidance literature:

Multi-step reaction with 2 steps

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

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

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

DOI:10.1021/ol035773h

upstream raw materials:

(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:

(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 (S)-2-pent-4-enoylamino-1-phenyl-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[5.2.1.0^1,5]dec-8-ene-6-carbonyl]-amino}-2-phenyl-ethyl ester

(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 (1S,2S)-3-methoxy-2-pent-4-enoylamino-1-phenyl-propyl ester

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

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