methyl (2S) 2-N-tert-butyloxycarbonyl-4-N-benzyloxycarbonyl-(2,4)-diaminobutyrate

Base Information

• Chemical Name: methyl (2S) 2-N-tert-butyloxycarbonyl-4-N-benzyloxycarbonyl-(2,4)-diaminobutyrate
• CAS No.: 226212-75-5
• Molecular Formula: C₁₈H₂₆N₂O₆
• Molecular Weight: 366.414

Synonyms:methyl (2S) 2-N-tert-butyloxycarbonyl-4-N-benzyloxycarbonyl-(2,4)-diaminobutyrate

Chemical Property of methyl (2S) 2-N-tert-butyloxycarbonyl-4-N-benzyloxycarbonyl-(2,4)-diaminobutyrate

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Technology Process of methyl (2S) 2-N-tert-butyloxycarbonyl-4-N-benzyloxycarbonyl-(2,4)-diaminobutyrate

There total 5 articles about methyl (2S) 2-N-tert-butyloxycarbonyl-4-N-benzyloxycarbonyl-(2,4)-diaminobutyrate 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: 93.0%

(2S)-4-(benzyloxycarbonyl)amino-2-(tert-butoxycarbonyl)aminobutyric acid (3350-20-7,47461-65-4,70882-68-7) + dimethyl sulfate (77-78-1) → methyl (2S) 2-N-tert-butyloxycarbonyl-4-N-benzyloxycarbonyl-(2,4)-diaminobutyrate (226212-75-5)

Guidance literature:

With potassium carbonate; In acetone; at 55 ℃; for 4h; Reflux;

DOI:10.1021/jo501639m

Reference yield: 51.0%

2-tert-butoxycarbonylamino-4-carboxyamino-butyric acid methyl ester + benzyl alcohol (100-51-6,185532-71-2) → methyl (2S) 2-N-tert-butyloxycarbonyl-4-N-benzyloxycarbonyl-(2,4)-diaminobutyrate (226212-75-5)

Guidance literature:

With diphenyl-phosphinic acid; triethylamine; In toluene; at 100 ℃;

DOI:10.1016/S0040-4020(99)00130-1

Reference yield:

(2S)-4-amino-2-[(tert-butoxycarbonyl)amino]butanoic acid (25691-37-6,80445-78-9) → methyl (2S) 2-N-tert-butyloxycarbonyl-4-N-benzyloxycarbonyl-(2,4)-diaminobutyrate (226212-75-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydrogencarbonate / water; acetone / 0.17 h / 0 °C

1.2: 0 - 20 °C

2.1: potassium carbonate / acetone / 4 h / 55 °C / Reflux

With sodium hydrogencarbonate; potassium carbonate; In water; acetone;

DOI:10.1021/jo501639m

upstream raw materials:

benzyl alcohol

Boc-Gln-OH

(2S)-4-(benzyloxycarbonyl)amino-2-(tert-butoxycarbonyl)aminobutyric acid

dimethyl sulfate

Downstream raw materials:

(S)-benzyl tert-butyl (4-hydroxybutane-1,3-diyl)dicarbamate

methyl (2S) 2-N-tosyl-2-N-tert-butylcarboxymethyl-4-N-benzyloxycarbonyl-(2,4)-diaminobutyrate

(2S) 2-N-tosyl-2-N-tert-butylcarboxymethyl-(2,4)-diaminobutyric acid

methyl (2S) 2-N-tosyl-4-N-benzyloxycarbonyl-(2,4)-diaminobutyrate

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