N^α-tert-butoxycarbonyl-L-alanyl-L-alanyl-(N^ε-benzyloxycarbonyl)-L-lysyl-L-alanyl-L-alanyl-(N^ε-(benzo-18-crown-6)-4-carbonyl)-L-lysyl-L-alanine methyl ester

Base Information

• Chemical Name: N^α-tert-butoxycarbonyl-L-alanyl-L-alanyl-(N^ε-benzyloxycarbonyl)-L-lysyl-L-alanyl-L-alanyl-(N^ε-(benzo-18-crown-6)-4-carbonyl)-L-lysyl-L-alanine methyl ester
• CAS No.: 155479-42-8
• Molecular Formula: C₅₈H₈₉N₉O₁₉
• Molecular Weight: 1216.39

Synonyms:N^α-tert-butoxycarbonyl-L-alanyl-L-alanyl-(N^ε-benzyloxycarbonyl)-L-lysyl-L-alanyl-L-alanyl-(N^ε-(benzo-18-crown-6)-4-carbonyl)-L-lysyl-L-alanine methyl ester

Chemical Property of N^α-tert-butoxycarbonyl-L-alanyl-L-alanyl-(N^ε-benzyloxycarbonyl)-L-lysyl-L-alanyl-L-alanyl-(N^ε-(benzo-18-crown-6)-4-carbonyl)-L-lysyl-L-alanine methyl ester

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Technology Process of N^α-tert-butoxycarbonyl-L-alanyl-L-alanyl-(N^ε-benzyloxycarbonyl)-L-lysyl-L-alanyl-L-alanyl-(N^ε-(benzo-18-crown-6)-4-carbonyl)-L-lysyl-L-alanine methyl ester

There total 9 articles about N^α-tert-butoxycarbonyl-L-alanyl-L-alanyl-(N^ε-benzyloxycarbonyl)-L-lysyl-L-alanyl-L-alanyl-(N^ε-(benzo-18-crown-6)-4-carbonyl)-L-lysyl-L-alanine methyl 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: 71.0%

Nα-tert-butoxycarbonyl-L-alanyl-L-alanyl-(Nε-benzyloxy-carbonyl)-L-lysyl-L-alanine (155479-41-7) + L-alanyl-(Nε-(benzo-18-crown-6)-4-carbonyl)-L-lysyl-L-alanine methyl ester hydrochloride → Nα-tert-butoxycarbonyl-L-alanyl-L-alanyl-(Nε-benzyloxycarbonyl)-L-lysyl-L-alanyl-L-alanyl-(Nε-(benzo-18-crown-6)-4-carbonyl)-L-lysyl-L-alanine methyl ester (155479-42-8)

Guidance literature:

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; for 18h;

DOI:10.1016/S0040-4020(01)80813-9

Reference yield:

Boc-Lys(Z)-Ala-OMe (22839-06-1) → Nα-tert-butoxycarbonyl-L-alanyl-L-alanyl-(Nε-benzyloxycarbonyl)-L-lysyl-L-alanyl-L-alanyl-(Nε-(benzo-18-crown-6)-4-carbonyl)-L-lysyl-L-alanine methyl ester (155479-42-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 4 N HCl / dioxane / 2 h / 25 °C

2: hydroxybenzotriazole*H₂O, dicyclohexylcarbodiimide

3: 98 percent / H₂ / 10percent Pd/C / methanol / 4 h / 2585.7 Torr

4: 93 percent / hydroxybenzotriazole*H₂O, dicyclohexylcarbodiimide / CH₂Cl₂ / 15 h / Ambient temperature

5: 96 percent / 4 N HCl / dioxane / 3 h / Ambient temperature

6: 71 percent / BOP, triethylamine / dimethylformamide / 18 h

With hydrogenchloride; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)80813-9

Reference yield:

Nα-tert-butoxycarbonyl-L-alanyl-(Nε-benzyloxy-carbonyl)-L-lysyl-L-alanine methyl ester (27909-29-1) → Nα-tert-butoxycarbonyl-L-alanyl-L-alanyl-(Nε-benzyloxycarbonyl)-L-lysyl-L-alanyl-L-alanyl-(Nε-(benzo-18-crown-6)-4-carbonyl)-L-lysyl-L-alanine methyl ester (155479-42-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / H₂ / 10percent Pd/C / methanol / 4 h / 2585.7 Torr

2: 93 percent / hydroxybenzotriazole*H₂O, dicyclohexylcarbodiimide / CH₂Cl₂ / 15 h / Ambient temperature

3: 96 percent / 4 N HCl / dioxane / 3 h / Ambient temperature

4: 71 percent / BOP, triethylamine / dimethylformamide / 18 h

With hydrogenchloride; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)80813-9

upstream raw materials:

N^α-tert-butoxycarbonyl-L-alanyl-L-alanyl-(N^ε-benzyloxy-carbonyl)-L-lysyl-L-alanine

Boc-Lys(Z)-OH

Boc-Lys(Z)-Ala-OMe

N^α-tert-butoxycarbonyl-L-alanyl-(N^ε-benzyloxy-carbonyl)-L-lysyl-L-alanine methyl ester

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