N-(tert-butyloxycarbonyl)-L-tyrosyl-O-tert-butyl-D-serylglycyl-L-phenylalanyl-L-leucyl-O-tert-butyl-L-threonine

Base Information

• Chemical Name: N-(tert-butyloxycarbonyl)-L-tyrosyl-O-tert-butyl-D-serylglycyl-L-phenylalanyl-L-leucyl-O-tert-butyl-L-threonine
• CAS No.: 78537-18-5
• Molecular Formula: C₄₆H₇₀N₆O₁₂
• Molecular Weight: 899.095

Synonyms:N-(tert-butyloxycarbonyl)-L-tyrosyl-O-tert-butyl-D-serylglycyl-L-phenylalanyl-L-leucyl-O-tert-butyl-L-threonine

Chemical Property of N-(tert-butyloxycarbonyl)-L-tyrosyl-O-tert-butyl-D-serylglycyl-L-phenylalanyl-L-leucyl-O-tert-butyl-L-threonine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of N-(tert-butyloxycarbonyl)-L-tyrosyl-O-tert-butyl-D-serylglycyl-L-phenylalanyl-L-leucyl-O-tert-butyl-L-threonine

There total 7 articles about N-(tert-butyloxycarbonyl)-L-tyrosyl-O-tert-butyl-D-serylglycyl-L-phenylalanyl-L-leucyl-O-tert-butyl-L-threonine 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: 85.0%

N-(tert-butyloxycarbonyl)-L-tyrosyl-O-tert-butyl-D-serylglycyl-L-phenylalanyl-L-leucyl-O-tert-butyl-L-threonine methyl ester (78537-17-4) → N-(tert-butyloxycarbonyl)-L-tyrosyl-O-tert-butyl-D-serylglycyl-L-phenylalanyl-L-leucyl-O-tert-butyl-L-threonine (78537-18-5)

Guidance literature:

With sodium hydroxide; In methanol; a) 0 deg C, 30 min, b) RT, 20 h;

DOI:10.1021/jm00142a002

Reference yield:

Boc-Tyr-OH (3978-80-1) → N-(tert-butyloxycarbonyl)-L-tyrosyl-O-tert-butyl-D-serylglycyl-L-phenylalanyl-L-leucyl-O-tert-butyl-L-threonine (78537-18-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 89 percent / triethylamine, 1-hydroxybenzotriazole (HOBT), dicyclohexylcarbodiimide (DCC) / tetrahydrofuran; CHCl₃ / a) 0 deg C, 1 h, b) RT, overnight

2: 94 percent / 1 N NaOH / methanol / a) 0 deg C, 30 min, b) RT, 2 h

3: 60 percent / triethylamine, 1-hydroxybenzotriazole (HOBT), dicyclohexylcarbodiimide (DCC) / tetrahydrofuran; CHCl₃ / a) 0 deg C, 1 h, b) RT, overnight

4: 80 percent / 1 N NaOH / methanol / a) 0 deg C, 1 h, b) RT, 20 h

5: 90 percent / triethylamine, 1-hydroxybenzotriazole (HOBT), dicyclohexylcarbodiimide (DCC) / tetrahydrofuran; CHCl₃ / a) 0 deg C, 1 h, b) RT, 20 h

6: 85 percent / 1 N NaOH / methanol / a) 0 deg C, 30 min, b) RT, 20 h

With sodium hydroxide; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; chloroform;

DOI:10.1021/jm00142a002

Reference yield:

O-tert-butyl-D-serine methyl ester hydrochloride (78537-14-1) → N-(tert-butyloxycarbonyl)-L-tyrosyl-O-tert-butyl-D-serylglycyl-L-phenylalanyl-L-leucyl-O-tert-butyl-L-threonine (78537-18-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 89 percent / triethylamine, 1-hydroxybenzotriazole (HOBT), dicyclohexylcarbodiimide (DCC) / tetrahydrofuran; CHCl₃ / a) 0 deg C, 1 h, b) RT, overnight

2: 94 percent / 1 N NaOH / methanol / a) 0 deg C, 30 min, b) RT, 2 h

3: 60 percent / triethylamine, 1-hydroxybenzotriazole (HOBT), dicyclohexylcarbodiimide (DCC) / tetrahydrofuran; CHCl₃ / a) 0 deg C, 1 h, b) RT, overnight

4: 80 percent / 1 N NaOH / methanol / a) 0 deg C, 1 h, b) RT, 20 h

5: 90 percent / triethylamine, 1-hydroxybenzotriazole (HOBT), dicyclohexylcarbodiimide (DCC) / tetrahydrofuran; CHCl₃ / a) 0 deg C, 1 h, b) RT, 20 h

6: 85 percent / 1 N NaOH / methanol / a) 0 deg C, 30 min, b) RT, 20 h

With sodium hydroxide; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; chloroform;

DOI:10.1021/jm00142a002

upstream raw materials:

N-(tert-butyloxycarbonyl)-L-tyrosyl-O-tert-butyl-D-serylglycyl-L-phenylalanyl-L-leucyl-O-tert-butyl-L-threonine methyl ester

Boc-Tyr-OH

O-tert-butyl-D-serine methyl ester hydrochloride

N-(tert-butyloxycarbonyl)-L-tyrosyl-O-tert-butyl-D-serine

Downstream raw materials:

[D-Ser(2)]-leucine enkephalin-Thr

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