N-benzyloxycarbonyl-O-benzyl-L-tyrosyl-2,L-Ser⁵-O-(11,33-tetraisopropyldisiloxane-1,3-diyl)-L-serylglycyl-L-phenylalanyl-L-serine> benzyl ester

Base Information

• Chemical Name: N-benzyloxycarbonyl-O-benzyl-L-tyrosyl-2,L-Ser⁵-O-(11,33-tetraisopropyldisiloxane-1,3-diyl)-L-serylglycyl-L-phenylalanyl-L-serine> benzyl ester
• CAS No.: 113247-71-5
• Molecular Formula: C₆₀H₇₇N₅O₁₂Si₂
• Molecular Weight: 1116.47

Synonyms:N-benzyloxycarbonyl-O-benzyl-L-tyrosyl-2,L-Ser⁵-O-(11,33-tetraisopropyldisiloxane-1,3-diyl)-L-serylglycyl-L-phenylalanyl-L-serine> benzyl ester

Chemical Property of N-benzyloxycarbonyl-O-benzyl-L-tyrosyl-2,L-Ser⁵-O-(11,33-tetraisopropyldisiloxane-1,3-diyl)-L-serylglycyl-L-phenylalanyl-L-serine> benzyl ester

Chemical Property:

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Technology Process of N-benzyloxycarbonyl-O-benzyl-L-tyrosyl-2,L-Ser⁵-O-(11,33-tetraisopropyldisiloxane-1,3-diyl)-L-serylglycyl-L-phenylalanyl-L-serine> benzyl ester

There total 19 articles about N-benzyloxycarbonyl-O-benzyl-L-tyrosyl-2,L-Ser⁵-O-(11,33-tetraisopropyldisiloxane-1,3-diyl)-L-serylglycyl-L-phenylalanyl-L-serine> 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: 31.0%

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane (69304-37-6) + N-benzyloxycarbonyl-O-benzyl-L-tyrosyl-O-t-butyl-L-serylglycyl-L-phenylalanyl-O-t-butyl-L-serine benzyl ester (113247-70-4) → N-benzyloxycarbonyl-O-benzyl-L-tyrosyl-2,L-Ser5-O-(11,33-tetraisopropyldisiloxane-1,3-diyl)-L-serylglycyl-L-phenylalanyl-L-serine> benzyl ester (113247-71-5)

Guidance literature:

In pyridine; for 144h;

Reference yield:

N-benzyloxycarbonyl-O-benzyl-L-tyrosine (86827-18-1,92455-53-3,16677-29-5) → N-benzyloxycarbonyl-O-benzyl-L-tyrosyl-2,L-Ser5-O-(11,33-tetraisopropyldisiloxane-1,3-diyl)-L-serylglycyl-L-phenylalanyl-L-serine> benzyl ester (113247-71-5)

Guidance literature:

Multi-step reaction with 4 steps

1: DCCI / tetrahydrofuran / 0 °C

2: N,N-di-isopropylethylamine / tetrahydrofuran / 0 deg C --> room temp., 2 h

3: 76 percent / TFA / CH₂Cl₂ / 1.5 h / Ambient temperature

4: 31 percent / pyridine / 144 h

With N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; pyridine; dichloromethane;

Reference yield:

N-fluorenylmethoxycarbonyl-O-t-butyl-L-serylglycyne benzyl ester (113247-73-7) → N-benzyloxycarbonyl-O-benzyl-L-tyrosyl-2,L-Ser5-O-(11,33-tetraisopropyldisiloxane-1,3-diyl)-L-serylglycyl-L-phenylalanyl-L-serine> benzyl ester (113247-71-5)

Guidance literature:

Multi-step reaction with 9 steps

1: DCCI / tetrahydrofuran / 0 °C

2: N,N-di-isopropylethylamine / tetrahydrofuran / 0 deg C --> room temp., 2 h

3: H₂ / Pd/C / ethanol; ethyl acetate / 1 h

4: DCCI / tetrahydrofuran / 0 °C

5: N-diisopropylethylamine / tetrahydrofuran / 0 deg C --> room temp., 2 h

6: piperidine / dimethylformamide / 0.17 h / Ambient temperature

7: N,N-di-isopropylethylamine / tetrahydrofuran / 0 deg C --> room temp., 2 h

8: 76 percent / TFA / CH₂Cl₂ / 1.5 h / Ambient temperature

9: 31 percent / pyridine / 144 h

With piperidine; hydrogen; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

upstream raw materials:

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane

N-benzyloxycarbonyl-O-benzyl-L-tyrosyl-O-t-butyl-L-serylglycyl-L-phenylalanyl-O-t-butyl-L-serine benzyl ester

L-Phenylalanine benzyl ester

N-benzyloxycarbonyl-O-benzyl-L-tyrosine

Downstream raw materials:

L-tyrosyl2,L-Ser⁵-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-L-serylglycyl-L-phenylalanyl-L-serine>

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