N-Boc-Thr-{[N^α-Cbz-N^γ-(4,4'-dimethoxybenzhydryl)-Asn]-D-Ala}-{N-[(4S)-4-amino-6-methyl-3-oxo-2-(triphenylphosphoranylidene)heptanoyl]-Leu}-OBn

Base Information

• Chemical Name: N-Boc-Thr-{[N^α-Cbz-N^γ-(4,4'-dimethoxybenzhydryl)-Asn]-D-Ala}-{N-[(4S)-4-amino-6-methyl-3-oxo-2-(triphenylphosphoranylidene)heptanoyl]-Leu}-OBn
• CAS No.: 221198-17-0
• Molecular Formula: C₇₈H₉₁N₆O₁₅P
• Molecular Weight: 1383.59

Synonyms:N-Boc-Thr-{[N^α-Cbz-N^γ-(4,4'-dimethoxybenzhydryl)-Asn]-D-Ala}-{N-[(4S)-4-amino-6-methyl-3-oxo-2-(triphenylphosphoranylidene)heptanoyl]-Leu}-OBn

Chemical Property of N-Boc-Thr-{[N^α-Cbz-N^γ-(4,4'-dimethoxybenzhydryl)-Asn]-D-Ala}-{N-[(4S)-4-amino-6-methyl-3-oxo-2-(triphenylphosphoranylidene)heptanoyl]-Leu}-OBn

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of N-Boc-Thr-{[N^α-Cbz-N^γ-(4,4'-dimethoxybenzhydryl)-Asn]-D-Ala}-{N-[(4S)-4-amino-6-methyl-3-oxo-2-(triphenylphosphoranylidene)heptanoyl]-Leu}-OBn

There total 12 articles about N-Boc-Thr-{[N^α-Cbz-N^γ-(4,4'-dimethoxybenzhydryl)-Asn]-D-Ala}-{N-[(4S)-4-amino-6-methyl-3-oxo-2-(triphenylphosphoranylidene)heptanoyl]-Leu}-OBn 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:

N-((S)-4-{[(tert-butoxy)carbonyl]amino}-6-methyl-3-oxo-2-(triphenylphosphoranylidene)heptanoyl)-Leu-OBn (221198-00-1) → N-Boc-Thr-{[Nα-Cbz-Nγ-(4,4'-dimethoxybenzhydryl)-Asn]-D-Ala}-{N-[(4S)-4-amino-6-methyl-3-oxo-2-(triphenylphosphoranylidene)heptanoyl]-Leu}-OBn (221198-17-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / N-[3-(dimethylamino)propyl]-N'-ethylcarbodiimide; 1-hydroxybenzotriazole; Et₃N / CH₂Cl₂ / 22 h / 0 - 23 °C

2: piperidine / dimethylformamide / 1 h / 23 °C

3: 4.40 g / N-[3-(dimethylamino)propyl]-N'-ethylcarbodiimide; 1-hydroxybenzotriazole; Et₃N / CH₂Cl₂ / 18 h / 0 - 23 °C

With piperidine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane; N,N-dimethyl-formamide; 1: Condensation / 2: Elimination / 3: Condensation;

DOI:10.1002/1522-2675(20000906)83:9<2607::AID-HLCA2607>3.0.CO;2-B

Reference yield:

{N-[2-(triphenylphosphonium)acetyl]-Leu-OBn} bromide → N-Boc-Thr-{[Nα-Cbz-Nγ-(4,4'-dimethoxybenzhydryl)-Asn]-D-Ala}-{N-[(4S)-4-amino-6-methyl-3-oxo-2-(triphenylphosphoranylidene)heptanoyl]-Leu}-OBn (221198-17-0)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / CH₂Cl₂

2: 9.08 g / 1,1'-carbonyldiimidazole / CH₂Cl₂ / 24 h / 23 °C

3: 78 percent / N-[3-(dimethylamino)propyl]-N'-ethylcarbodiimide; 1-hydroxybenzotriazole; Et₃N / CH₂Cl₂ / 22 h / 0 - 23 °C

4: piperidine / dimethylformamide / 1 h / 23 °C

5: 4.40 g / N-[3-(dimethylamino)propyl]-N'-ethylcarbodiimide; 1-hydroxybenzotriazole; Et₃N / CH₂Cl₂ / 18 h / 0 - 23 °C

With piperidine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; 1,1'-carbonyldiimidazole; In dichloromethane; N,N-dimethyl-formamide; 1: Elimination / 2: Condensation / 3: Condensation / 4: Elimination / 5: Condensation;

DOI:10.1002/1522-2675(20000906)83:9<2607::AID-HLCA2607>3.0.CO;2-B

Reference yield:

N-Boc-Thr[N-Fmoc-D-Ala]-{N-[(4S)-4-amino-6-methyl-3-oxo-2-(triphenylphosphoranylidene)heptanoyl]-Leu}-OBn (221198-10-3) → N-Boc-Thr-{[Nα-Cbz-Nγ-(4,4'-dimethoxybenzhydryl)-Asn]-D-Ala}-{N-[(4S)-4-amino-6-methyl-3-oxo-2-(triphenylphosphoranylidene)heptanoyl]-Leu}-OBn (221198-17-0)

Guidance literature:

Multi-step reaction with 2 steps

1: piperidine / dimethylformamide / 1 h / 23 °C

2: 4.40 g / N-[3-(dimethylamino)propyl]-N'-ethylcarbodiimide; 1-hydroxybenzotriazole; Et₃N / CH₂Cl₂ / 18 h / 0 - 23 °C

With piperidine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane; N,N-dimethyl-formamide; 1: Elimination / 2: Condensation;

DOI:10.1002/1522-2675(20000906)83:9<2607::AID-HLCA2607>3.0.CO;2-B

upstream raw materials:

N^α-Cbz-N^γ-(4,4'-dimethoxybenzhydryl)-Asn-OH

L-Leucine benzyl ester

N-(tert-butyloxycarbonyl)-threonine benzyl ester

N-(2-bromoacetyl)-L-leucine benzyl ester

Downstream raw materials:

YM-47141

N-Boc-Thr-{N-[(4S)-4-amino-6-methyl-3-oxo-2-(triphenylphosphoranylidene)heptanoyl]-Leu}-[N^γ-(4,4'-dimethyloxybenzhydryl)-Asn]-D-Ala (threonine hydroxy) lactone

N-[N(isopropylacetyl)-Phe-Thr]-Thr-{N-[(4S)-4-amino-6-methyl-3-oxo-2-(triphenylphosphoranylidene)heptanoyl]-Leu}-Asn-D-Ala (threonine hydroxy) lactone

N-[N(phenylacetyl)-Phe-Thr]-Thr-{N-[(4S)-4-amino-6-methyl-3-oxo-2-(triphenylphosphoranylidene)heptanoyl]-Leu}-Asn-D-Ala (threonine hydroxy) lactone

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