(S)-2-{(S)-2-[(S)-2-(benzyloxycarbonylamino)-5-(tertbutoxycarbonylamino)valerylamino]-5-(tert-butoxycarbonylamino)valerylamino}-5-(tert-butoxycarbonylamino)valeric acid

Base Information

• Chemical Name: (S)-2-{(S)-2-[(S)-2-(benzyloxycarbonylamino)-5-(tertbutoxycarbonylamino)valerylamino]-5-(tert-butoxycarbonylamino)valerylamino}-5-(tert-butoxycarbonylamino)valeric acid
• CAS No.: 250215-13-5
• Molecular Formula: C₃₈H₆₂N₆O₁₂
• Molecular Weight: 794.943

Synonyms:(S)-2-{(S)-2-[(S)-2-(benzyloxycarbonylamino)-5-(tertbutoxycarbonylamino)valerylamino]-5-(tert-butoxycarbonylamino)valerylamino}-5-(tert-butoxycarbonylamino)valeric acid

Chemical Property of (S)-2-{(S)-2-[(S)-2-(benzyloxycarbonylamino)-5-(tertbutoxycarbonylamino)valerylamino]-5-(tert-butoxycarbonylamino)valerylamino}-5-(tert-butoxycarbonylamino)valeric acid

Chemical Property:

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Technology Process of (S)-2-{(S)-2-[(S)-2-(benzyloxycarbonylamino)-5-(tertbutoxycarbonylamino)valerylamino]-5-(tert-butoxycarbonylamino)valerylamino}-5-(tert-butoxycarbonylamino)valeric acid

There total 6 articles about (S)-2-{(S)-2-[(S)-2-(benzyloxycarbonylamino)-5-(tertbutoxycarbonylamino)valerylamino]-5-(tert-butoxycarbonylamino)valerylamino}-5-(tert-butoxycarbonylamino)valeric 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:

Z-Orn(Boc)-OH (7733-29-1,199924-46-4) → (S)-2-{(S)-2-[(S)-2-(benzyloxycarbonylamino)-5-(tertbutoxycarbonylamino)valerylamino]-5-(tert-butoxycarbonylamino)valerylamino}-5-(tert-butoxycarbonylamino)valeric acid (250215-13-5)

Guidance literature:

Multi-step reaction with 4 steps

1: dicyclohexylcarbodiimide / tetrahydrofuran / 10 h / 20 °C

2: NaHCO₃ / H₂O; tetrahydrofuran / 6 h / 20 °C

3: dicyclohexylcarbodiimide / tetrahydrofuran

4: NaHCO₃ / H₂O; tetrahydrofuran

With sodium hydrogencarbonate; dicyclohexyl-carbodiimide; In tetrahydrofuran; water; 1: Esterification / 2: Substitution / 3: Esterification / 4: Substitution;

DOI:10.1021/jo990769y

Reference yield:

(S)-2-Benzyloxycarbonylamino-5-tert-butoxycarbonylamino-pentanoic acid 2,5-dioxo-pyrrolidin-1-yl ester (116115-11-8) → (S)-2-{(S)-2-[(S)-2-(benzyloxycarbonylamino)-5-(tertbutoxycarbonylamino)valerylamino]-5-(tert-butoxycarbonylamino)valerylamino}-5-(tert-butoxycarbonylamino)valeric acid (250215-13-5)

Guidance literature:

Multi-step reaction with 3 steps

1: NaHCO₃ / H₂O; tetrahydrofuran / 6 h / 20 °C

2: dicyclohexylcarbodiimide / tetrahydrofuran

3: NaHCO₃ / H₂O; tetrahydrofuran

With sodium hydrogencarbonate; dicyclohexyl-carbodiimide; In tetrahydrofuran; water; 1: Substitution / 2: Esterification / 3: Substitution;

DOI:10.1021/jo990769y

Reference yield:

(S)-2-[(S)-2-(benzyloxycarbonylamino)-5-(tert-butoxycarbonylamino)valerylamino]-5-(tert-butoxycarbonylamino)valeric acid (32393-54-7) → (S)-2-{(S)-2-[(S)-2-(benzyloxycarbonylamino)-5-(tertbutoxycarbonylamino)valerylamino]-5-(tert-butoxycarbonylamino)valerylamino}-5-(tert-butoxycarbonylamino)valeric acid (250215-13-5)

Guidance literature:

Multi-step reaction with 2 steps

1: dicyclohexylcarbodiimide / tetrahydrofuran

2: NaHCO₃ / H₂O; tetrahydrofuran

With sodium hydrogencarbonate; dicyclohexyl-carbodiimide; In tetrahydrofuran; water; 1: Esterification / 2: Substitution;

DOI:10.1021/jo990769y

upstream raw materials:

N^δ-(tert-butoxycarbonyl)-L-ornithine

Z-Orn(Boc)-OH

(S)-2-Benzyloxycarbonylamino-5-tert-butoxycarbonylamino-pentanoic acid 2,5-dioxo-pyrrolidin-1-yl ester

(S)-2-[(S)-2-(benzyloxycarbonylamino)-5-(tert-butoxycarbonylamino)valerylamino]-5-(tert-butoxycarbonylamino)valeric acid

Downstream raw materials:

(S)-2-((S)-2-((S)-2-Benzyloxycarbonylamino-5-{[1-phenyl-meth-(E)-ylidene]-amino}-pentanoylamino)-5-{[1-phenyl-meth-(E)-ylidene]-amino}-pentanoylamino)-5-{[1-phenyl-meth-(E)-ylidene]-amino}-pentanoic acid

N²-Z-N⁵-acetyl-N⁵-O-acetyl-L-ornithyl-N⁵-acetyl-N⁵-O-acetyl-L-ornithyl-N⁵-acetyl-N⁵-O-acetyl-L-ornithine

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