<<4(S)-methyl-3(S)-<(N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-D-phenylglycyl)amino>-2-oxo-1-azetidinyl>oxy>acetic acid

Base Information

• Chemical Name: <<4(S)-methyl-3(S)-<(N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-D-phenylglycyl)amino>-2-oxo-1-azetidinyl>oxy>acetic acid
• CAS No.: 131080-76-7
• Molecular Formula: C₃₅H₅₃N₉O₁₄
• Molecular Weight: 823.858

Synonyms:<<4(S)-methyl-3(S)-<(N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-D-phenylglycyl)amino>-2-oxo-1-azetidinyl>oxy>acetic acid

Chemical Property of <<4(S)-methyl-3(S)-<(N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-D-phenylglycyl)amino>-2-oxo-1-azetidinyl>oxy>acetic acid

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Technology Process of <<4(S)-methyl-3(S)-<(N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-D-phenylglycyl)amino>-2-oxo-1-azetidinyl>oxy>acetic acid

There total 10 articles about <<4(S)-methyl-3(S)-<(N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-D-phenylglycyl)amino>-2-oxo-1-azetidinyl>oxy>acetic 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: 95.0%

benzyl <<4(S)-methyl-3(S)-<5-acetyl-N5-(benzyloxy)-N2-(benzyloxycarbonyl)-L-ornithyl-N5-acetyl-N5-(benzyloxy)-L-ornithyl-N5-acetyl-N5-(benzyloxy)-L-ornithyl-D-phenylglycyl>amino>-2-oxo-1-azetidinyl>oxy>acetate (131080-82-5) → <<4(S)-methyl-3(S)-<(N5-acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithyl-D-phenylglycyl)amino>-2-oxo-1-azetidinyl>oxy>acetic acid (131080-76-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In water; ethyl acetate; for 1h;

DOI:10.1021/jm00107a014

Reference yield:

(R)-phenylglycine (875-74-1) → <<4(S)-methyl-3(S)-<(N5-acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithyl-D-phenylglycyl)amino>-2-oxo-1-azetidinyl>oxy>acetic acid (131080-76-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 99 percent / potassium bicarbonate / H₂O; tetrahydrofuran / 18 h

2: 98 percent / dicyclohexylcarbodiimide (DCC) / tetrahydrofuran / 43 h

3: potassium bicarbonate / H₂O; ethyl acetate

4: trifluoroacetic acid / CH₂Cl₂ / 2.5 h

5: potassium bicarbonate / H₂O; ethyl acetate

6: 95 percent / H₂ / 10percent Pd/C / H₂O; ethyl acetate / 1 h

With hydrogen; potassium hydrogencarbonate; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate;

DOI:10.1021/jm00107a014

Reference yield:

Boc-D-Phg-OH (33125-05-2) → <<4(S)-methyl-3(S)-<(N5-acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithyl-D-phenylglycyl)amino>-2-oxo-1-azetidinyl>oxy>acetic acid (131080-76-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / dicyclohexylcarbodiimide (DCC) / tetrahydrofuran / 43 h

2: potassium bicarbonate / H₂O; ethyl acetate

3: trifluoroacetic acid / CH₂Cl₂ / 2.5 h

4: potassium bicarbonate / H₂O; ethyl acetate

5: 95 percent / H₂ / 10percent Pd/C / H₂O; ethyl acetate / 1 h

With hydrogen; potassium hydrogencarbonate; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate;

DOI:10.1021/jm00107a014

upstream raw materials:

benzyl <<4(S)-methyl-3(S)-<5-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-D-phenylglycyl>amino>-2-oxo-1-azetidinyl>oxy>acetate

(R)-phenylglycine

Boc-D-Phg-OH

(N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl)-(N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl)-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithine

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