(S)-3-Benzyloxycarbonylamino-N-{[(1R,2S,3S,6S,7R)-(4-oxa-tricyclo[4.2.1.0^3,7]non-2-yl)oxycarbonyl]-phenyl-methyl}-succinamic acid benzyl ester

Base Information

• Chemical Name: (S)-3-Benzyloxycarbonylamino-N-{[(1R,2S,3S,6S,7R)-(4-oxa-tricyclo[4.2.1.0^3,7]non-2-yl)oxycarbonyl]-phenyl-methyl}-succinamic acid benzyl ester
• CAS No.: 124442-01-9
• Molecular Formula: C₃₅H₃₆N₂O₈
• Molecular Weight: 612.679

Synonyms:

Chemical Property of (S)-3-Benzyloxycarbonylamino-N-{[(1R,2S,3S,6S,7R)-(4-oxa-tricyclo[4.2.1.0^3,7]non-2-yl)oxycarbonyl]-phenyl-methyl}-succinamic acid benzyl ester

Chemical Property:

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Useful:

Technology Process of (S)-3-Benzyloxycarbonylamino-N-{[(1R,2S,3S,6S,7R)-(4-oxa-tricyclo[4.2.1.0^3,7]non-2-yl)oxycarbonyl]-phenyl-methyl}-succinamic acid benzyl ester

There total 4 articles about (S)-3-Benzyloxycarbonylamino-N-{[(1R,2S,3S,6S,7R)-(4-oxa-tricyclo[4.2.1.0^3,7]non-2-yl)oxycarbonyl]-phenyl-methyl}-succinamic acid benzyl 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:

(+/-)-3a,3aβ,5a,6β,6aβ-hexahydro-3,5-methano-2H-cyclopenta<6>furan-6-ol (94942-48-0,124510-32-3,18684-64-5) → (S)-3-Benzyloxycarbonylamino-N-{[(1R,2S,3S,6S,7R)-(4-oxa-tricyclo[4.2.1.03,7]non-2-yl)oxycarbonyl]-phenyl-methyl}-succinamic acid benzyl ester (124442-01-9,124510-71-0)

Guidance literature:

Multi-step reaction with 3 steps

1: dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1.) -78 deg C, 0.5 h, 2.) -23 deg C

2: 5N HCl / acetone

3: tetrahydrofuran / 24 h

With hydrogenchloride; dmap; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; acetone;

DOI:10.1021/jm00165a027

Reference yield:

(R)-phenylglycine (875-74-1) → (S)-3-Benzyloxycarbonylamino-N-{[(1R,2S,3S,6S,7R)-(4-oxa-tricyclo[4.2.1.03,7]non-2-yl)oxycarbonyl]-phenyl-methyl}-succinamic acid benzyl ester (124442-01-9,124510-71-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 62 percent / 2N NaOH / dioxane / 2 h

2: dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1.) -78 deg C, 0.5 h, 2.) -23 deg C

3: 5N HCl / acetone

4: tetrahydrofuran / 24 h

With hydrogenchloride; dmap; sodium hydroxide; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; acetone;

DOI:10.1021/jm00165a027

Reference yield:

N-<(o-nitrophenyl)sulfenyl>-D-phenylglycine (16679-41-7) → (S)-3-Benzyloxycarbonylamino-N-{[(1R,2S,3S,6S,7R)-(4-oxa-tricyclo[4.2.1.03,7]non-2-yl)oxycarbonyl]-phenyl-methyl}-succinamic acid benzyl ester (124442-01-9,124510-71-0)

Guidance literature:

Multi-step reaction with 3 steps

1: dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1.) -78 deg C, 0.5 h, 2.) -23 deg C

2: 5N HCl / acetone

3: tetrahydrofuran / 24 h

With hydrogenchloride; dmap; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; acetone;

DOI:10.1021/jm00165a027

upstream raw materials:

(+/-)-3a,3aβ,5a,6β,6aβ-hexahydro-3,5-methano-2H-cyclopenta<6>furan-6-ol

(R)-phenylglycine

N-<(o-nitrophenyl)sulfenyl>-D-phenylglycine

(2-Nitro-phenylsulfanylamino)-phenyl-acetic acid (1R,2S,3S,6S,7R)-(4-oxa-tricyclo[4.2.1.0^3,7]non-2-yl) ester

Downstream raw materials:

(S)-3-Amino-N-{[(1R,2S,3S,6S,7R)-(4-oxa-tricyclo[4.2.1.0^3,7]non-2-yl)oxycarbonyl]-phenyl-methyl}-succinamic acid

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