tert-butyl (3S)-N-(benzyloxycarbonyl)-3-amino-4-methylpentanoate

Base Information

• Chemical Name: tert-butyl (3S)-N-(benzyloxycarbonyl)-3-amino-4-methylpentanoate
• CAS No.: 245323-40-4
• Molecular Formula: C₁₈H₂₇NO₄
• Molecular Weight: 321.417
• Mol file: 245323-40-4.mol

Synonyms:tert-butyl (3S)-N-(benzyloxycarbonyl)-3-amino-4-methylpentanoate

Chemical Property of tert-butyl (3S)-N-(benzyloxycarbonyl)-3-amino-4-methylpentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (3S)-N-(benzyloxycarbonyl)-3-amino-4-methylpentanoate

There total 5 articles about tert-butyl (3S)-N-(benzyloxycarbonyl)-3-amino-4-methylpentanoate 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: 76.0%

(S)-4-(tert-butoxy)-2-(1-methylethyl)-4-oxobutanoic acid (134807-43-5) + benzyl alcohol (100-51-6,185532-71-2) → tert-butyl (3S)-N-(benzyloxycarbonyl)-3-amino-4-methylpentanoate (245323-40-4)

Guidance literature:

With diphenyl-phosphinic acid; triethylamine; In toluene; for 24h; Heating;

DOI:10.1021/jo990756k

Reference yield: 63.0%

1-diazo-2-oxo-(3R)-3-benzyloxycarbonylamino-4-methylpentane (28094-73-7) + tert-butyl alcohol (75-65-0) → tert-butyl (3S)-N-(benzyloxycarbonyl)-3-amino-4-methylpentanoate (245323-40-4)

Guidance literature:

With silver benzoate; triethylamine; at 70 ℃; for 4h; Darkness; Inert atmosphere;

DOI:10.1021/np100877h

Reference yield:

bromoacetic acid tert-butyl ester (5292-43-3) → tert-butyl (3S)-N-(benzyloxycarbonyl)-3-amino-4-methylpentanoate (245323-40-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / NaN(SiMe₃)2 / tetrahydrofuran / 6 h / -78 °C

2: 84 percent / H₂O₂; LiOH / tetrahydrofuran; H₂O / 7 h / 0 °C

3: 76 percent / Et₃N; DPPA / toluene / 24 h / Heating

With lithium hydroxide; diphenyl-phosphinic acid; dihydrogen peroxide; sodium hexamethyldisilazane; triethylamine; In tetrahydrofuran; water; toluene; 1: Alkylation / 2: Hydrolysis / 3: Rearrangement;

DOI:10.1021/jo990756k

upstream raw materials:

(S)-4-(tert-butoxy)-2-(1-methylethyl)-4-oxobutanoic acid

benzyl alcohol

bromoacetic acid tert-butyl ester

(4S)-3-((2S)-4-(tert-butoxy)-2-(1-methylethyl)-4-oxobutanoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one

Downstream raw materials:

C₁₅H₂₁NO₄

C₁₉H₂₉NO₄

(3S)-N-(benzyloxycarbonyl)-3-amino-4-methylpentanoic acid