{2-tert-Butoxycarbonylamino-3-[3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionylamino}-(dimethoxy-phosphoryl)-acetic acid methyl ester

Base Information

• Chemical Name: {2-tert-Butoxycarbonylamino-3-[3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionylamino}-(dimethoxy-phosphoryl)-acetic acid methyl ester
• CAS No.: 121057-01-0
• Molecular Formula: C₃₇H₇₁N₂O₁₁PSi₃
• Molecular Weight: 835.208

Synonyms:

Chemical Property of {2-tert-Butoxycarbonylamino-3-[3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionylamino}-(dimethoxy-phosphoryl)-acetic acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of {2-tert-Butoxycarbonylamino-3-[3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionylamino}-(dimethoxy-phosphoryl)-acetic acid methyl ester

There total 12 articles about {2-tert-Butoxycarbonylamino-3-[3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionylamino}-(dimethoxy-phosphoryl)-acetic acid 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:

di-tert-butyl dicarbonate (24424-99-5) → {2-tert-Butoxycarbonylamino-3-[3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionylamino}-(dimethoxy-phosphoryl)-acetic acid methyl ester (121057-01-0,121057-00-9)

Guidance literature:

Multi-step reaction with 6 steps

1: CH₂Cl₂

2: 83 percent / 1 N KOH / 0.25 h

3: 75 percent / DBU / acetonitrile / 2 h / Ambient temperature

4: 1) NaH / 1.) THF, room temp., 20 min, 2.) 5 h

5: 92 percent / H₂ / 5percent Pd-C / methanol / 12 h / 760 Torr

6: dicyclohexylcarbodiimide / CH₂Cl₂; dimethylformamide / 4 h / Ambient temperature

With potassium hydroxide; hydrogen; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja00198a040

Reference yield:

methyl galloate (99-24-1) → {2-tert-Butoxycarbonylamino-3-[3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionylamino}-(dimethoxy-phosphoryl)-acetic acid methyl ester (121057-01-0,121057-00-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / imidazole / dimethylformamide / 20 h

2: 79 percent / LiAlH₄ / tetrahydrofuran / 3 h / Heating

3: 75 percent / pyridinium chlorochromate / CH₂Cl₂ / 4 h / Ambient temperature

4: 1) NaH / 1.) THF, room temp., 20 min, 2.) 5 h

5: 92 percent / H₂ / 5percent Pd-C / methanol / 12 h / 760 Torr

6: dicyclohexylcarbodiimide / CH₂Cl₂; dimethylformamide / 4 h / Ambient temperature

With 1H-imidazole; lithium aluminium tetrahydride; hydrogen; sodium hydride; dicyclohexyl-carbodiimide; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00198a040

Reference yield:

N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester (100945-15-1,88568-95-0) → {2-tert-Butoxycarbonylamino-3-[3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionylamino}-(dimethoxy-phosphoryl)-acetic acid methyl ester (121057-01-0,121057-00-9)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / 5percent Pd-C / methanol / 0.75 h / 760 Torr

2: dicyclohexylcarbodiimide / CH₂Cl₂; dimethylformamide / 4 h / Ambient temperature

With hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00198a040

upstream raw materials:

methyl 2-amino-2-(dimethoxyphosphoryl)acetate

N-BOC-TBDMS-5-hydroxy-Dopa

di-tert-butyl dicarbonate

methyl galloate

Downstream raw materials:

{2-tert-Butoxycarbonylamino-3-[3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionylamino}-(dimethoxy-phosphoryl)-acetic acid

({2-tert-Butoxycarbonylamino-3-[3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionylamino}-{(E)-2-[3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-phenyl]-vinylcarbamoyl}-methyl)-phosphonic acid dimethyl ester

({2-tert-Butoxycarbonylamino-3-[3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionylamino}-{2-(4-nitro-phenylselanyl)-2-[3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-phenyl]-ethylcarbamoyl}-methyl)-phosphonic acid dimethyl ester

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