N-<(tert-butyloxycarbonyl)-L-valyl>-(2R,4RS,5S)-4-acetoxy-5-amino-2-benzyl-7-methyloctanoic acid

Base Information

• Chemical Name: N-<(tert-butyloxycarbonyl)-L-valyl>-(2R,4RS,5S)-4-acetoxy-5-amino-2-benzyl-7-methyloctanoic acid
• CAS No.: 105943-66-6
• Molecular Formula: C₂₈H₄₄N₂O₇
• Molecular Weight: 520.667
• Mol file: 105943-66-6.mol

Synonyms:

Chemical Property of N-<(tert-butyloxycarbonyl)-L-valyl>-(2R,4RS,5S)-4-acetoxy-5-amino-2-benzyl-7-methyloctanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-<(tert-butyloxycarbonyl)-L-valyl>-(2R,4RS,5S)-4-acetoxy-5-amino-2-benzyl-7-methyloctanoic acid

There total 9 articles about N-<(tert-butyloxycarbonyl)-L-valyl>-(2R,4RS,5S)-4-acetoxy-5-amino-2-benzyl-7-methyloctanoic acid 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:

(R)-2-<(phenylmethoxy)methyl>-3-benzenepropanol (88481-75-8) → N-<(tert-butyloxycarbonyl)-L-valyl>-(2R,4RS,5S)-4-acetoxy-5-amino-2-benzyl-7-methyloctanoic acid (105943-66-6,106032-70-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 80 percent / PPh₃, NBS / CH₂Cl₂ / 15 h / Ambient temperature

2: 1.) Mg / 1.) THF, 4 h, 2.) THF, RT, 4 h

3: HCl / dioxane / 0.5 h

4: NEt₃ / CH₂Cl₂ / 6 h / 0 °C

5: 100 percent / NEt₃, 4-(dimethylamino)pyridine / ethyl acetate / 5 h / Ambient temperature

6: 95 percent / HCOONH₂, AcOH / 10percent Pd/C / propan-2-ol

7: pyridinium dichromate / dimethylformamide / 35 h

With hydrogenchloride; dmap; N-Bromosuccinimide; dipyridinium dichromate; HCOONH₂; magnesium; acetic acid; triethylamine; triphenylphosphine; palladium on activated charcoal; In 1,4-dioxane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol;

Reference yield:

(4R,5S)-3-(3-phenylpropionyl)-4-methyl-5-phenyl-oxazolidin-2-one (95841-14-8) → N-<(tert-butyloxycarbonyl)-L-valyl>-(2R,4RS,5S)-4-acetoxy-5-amino-2-benzyl-7-methyloctanoic acid (105943-66-6,106032-70-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) LiN(Me₃Si)2 / 1.) THF, -78 deg C, 0.5 h, 2.) THF, from -78 deg C to 0 deg C, 5.5 h

2: 90 percent / Ca(BH₄)2 / ethanol; tetrahydrofuran / 0 °C

3: 80 percent / PPh₃, NBS / CH₂Cl₂ / 15 h / Ambient temperature

4: 1.) Mg / 1.) THF, 4 h, 2.) THF, RT, 4 h

5: HCl / dioxane / 0.5 h

6: NEt₃ / CH₂Cl₂ / 6 h / 0 °C

7: 100 percent / NEt₃, 4-(dimethylamino)pyridine / ethyl acetate / 5 h / Ambient temperature

8: 95 percent / HCOONH₂, AcOH / 10percent Pd/C / propan-2-ol

9: pyridinium dichromate / dimethylformamide / 35 h

With hydrogenchloride; dmap; N-Bromosuccinimide; dipyridinium dichromate; calcium borohydride; HCOONH₂; magnesium; acetic acid; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol;

Reference yield:

(2S)-2-benzyl-3-(benzyloxy)-1-bromopropane (105943-56-4) → N-<(tert-butyloxycarbonyl)-L-valyl>-(2R,4RS,5S)-4-acetoxy-5-amino-2-benzyl-7-methyloctanoic acid (105943-66-6,106032-70-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) Mg / 1.) THF, 4 h, 2.) THF, RT, 4 h

2: HCl / dioxane / 0.5 h

3: NEt₃ / CH₂Cl₂ / 6 h / 0 °C

4: 100 percent / NEt₃, 4-(dimethylamino)pyridine / ethyl acetate / 5 h / Ambient temperature

5: 95 percent / HCOONH₂, AcOH / 10percent Pd/C / propan-2-ol

6: pyridinium dichromate / dimethylformamide / 35 h

With hydrogenchloride; dmap; dipyridinium dichromate; HCOONH₂; magnesium; acetic acid; triethylamine; palladium on activated charcoal; In 1,4-dioxane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol;

upstream raw materials:

N-<(tert-butyloxycarbonyl)-L-valyl>-(2R,4RS,5S)-4-acetoxy-5-amino-2-benzyl-7-methyloctan-1-ol

(R)-2-<(phenylmethoxy)methyl>-3-benzenepropanol

(4R,5S)-3-(3-phenylpropionyl)-4-methyl-5-phenyl-oxazolidin-2-one

(2S)-2-benzyl-3-(benzyloxy)-1-bromopropane

Downstream raw materials:

(2R,4S,5S)-2-Benzyl-4-hydroxy-7-methyl-5-[(S)-3-methyl-2-(3-methyl-butyrylamino)-butyrylamino]-octanoic acid [(S)-1-(3-methyl-butylcarbamoyl)-ethyl]-amide

(2S,4S,5S)-2-Benzyl-4-hydroxy-7-methyl-5-[(S)-3-methyl-2-(3-methyl-butyrylamino)-butyrylamino]-octanoic acid [(S)-1-(3-methyl-butylcarbamoyl)-ethyl]-amide