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

Base Information

• Chemical Name: 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
• CAS No.: 221198-22-7
• Molecular Formula: C₆₃H₇₇N₆O₁₂P
• Molecular Weight: 1141.31

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 15 articles about 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 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-{N-[(4S)-4-amino-6-methyl-3-oxo-2-(triphenylphosphoranylidene)heptanoyl]-Leu}-[Nγ-(4,4'-dimethyloxybenzhydryl)-Asn]-D-Ala (threonine hydroxy) lactone (221198-22-7)

Guidance literature:

Multi-step reaction with 5 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

4: H₂ / Pd/C / methanol / 24 h / 23 °C / 760 Torr

5: 1.70 g / diphenylphosphoryl azide; NaHCO₃ / dimethylformamide / 72 h / 0 °C

With piperidine; diphenylphosphoranyl azide; hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Condensation / 2: Elimination / 3: Condensation / 4: Hydrogenolysis / 5: Cyclization;

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-{N-[(4S)-4-amino-6-methyl-3-oxo-2-(triphenylphosphoranylidene)heptanoyl]-Leu}-[Nγ-(4,4'-dimethyloxybenzhydryl)-Asn]-D-Ala (threonine hydroxy) lactone (221198-22-7)

Guidance literature:

Multi-step reaction with 7 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

6: H₂ / Pd/C / methanol / 24 h / 23 °C / 760 Torr

7: 1.70 g / diphenylphosphoryl azide; NaHCO₃ / dimethylformamide / 72 h / 0 °C

With piperidine; diphenylphosphoranyl azide; hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; 1,1'-carbonyldiimidazole; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Elimination / 2: Condensation / 3: Condensation / 4: Elimination / 5: Condensation / 6: Hydrogenolysis / 7: Cyclization;

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

Reference yield:

N-Boc-Thr-D-Ala-{N-[(4S)-4-amino-6-methyl-3-oxo-2-(triphenylphosphoranylidene)heptanoyl]-Leu}-OBn → N-Boc-Thr-{N-[(4S)-4-amino-6-methyl-3-oxo-2-(triphenylphosphoranylidene)heptanoyl]-Leu}-[Nγ-(4,4'-dimethyloxybenzhydryl)-Asn]-D-Ala (threonine hydroxy) lactone (221198-22-7)

Guidance literature:

Multi-step reaction with 3 steps

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

2: H₂ / Pd/C / methanol / 24 h / 23 °C / 760 Torr

3: 1.70 g / diphenylphosphoryl azide; NaHCO₃ / dimethylformamide / 72 h / 0 °C

With diphenylphosphoranyl azide; hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Condensation / 2: Hydrogenolysis / 3: Cyclization;

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

upstream raw materials:

L-Leucine benzyl ester

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

N-(tert-butyloxycarbonyl)-threonine benzyl ester

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

Downstream raw materials:

YM-47141

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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