(2R,4S,5S)-5-amino-6-(3,5-difluorobenzyloxy)-4-hydroxy-2-methylhexanoic acid ((S)-1-benzylcarbamoyl-2-methylpropyl)amide

Base Information

• Chemical Name: (2R,4S,5S)-5-amino-6-(3,5-difluorobenzyloxy)-4-hydroxy-2-methylhexanoic acid ((S)-1-benzylcarbamoyl-2-methylpropyl)amide
• CAS No.: 1067648-45-6
• Molecular Formula: C₂₆H₃₅F₂N₃O₄
• Molecular Weight: 491.578

Synonyms:(2R,4S,5S)-5-amino-6-(3,5-difluorobenzyloxy)-4-hydroxy-2-methylhexanoic acid ((S)-1-benzylcarbamoyl-2-methylpropyl)amide

Chemical Property of (2R,4S,5S)-5-amino-6-(3,5-difluorobenzyloxy)-4-hydroxy-2-methylhexanoic acid ((S)-1-benzylcarbamoyl-2-methylpropyl)amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4S,5S)-5-amino-6-(3,5-difluorobenzyloxy)-4-hydroxy-2-methylhexanoic acid ((S)-1-benzylcarbamoyl-2-methylpropyl)amide

There total 8 articles about (2R,4S,5S)-5-amino-6-(3,5-difluorobenzyloxy)-4-hydroxy-2-methylhexanoic acid ((S)-1-benzylcarbamoyl-2-methylpropyl)amide 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:

2,3-dideoxy-2-methyl-D-glucono-1,4-lactone (1067648-41-2) → (2R,4S,5S)-5-amino-6-(3,5-difluorobenzyloxy)-4-hydroxy-2-methylhexanoic acid ((S)-1-benzylcarbamoyl-2-methylpropyl)amide (1067648-45-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: di(n-butyl)tin oxide / toluene / 5 h / Reflux

1.2: 90 °C

2.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / -15 - 0 °C

2.2: 0 - 20 °C

3.1: 2-hydroxypyridin; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 96 h / Reflux

4.1: water; triphenylphosphine / methanol / 20 °C

With 2-hydroxypyridin; di-isopropyl azodicarboxylate; water; di(n-butyl)tin oxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; toluene;

DOI:10.1016/j.ejmech.2009.11.013

Reference yield:

2,3-dideoxy-6-O-(3,5-difluorobenzyl)-2-methyl-D-glucono-1,4-lactone (1067648-42-3) → (2R,4S,5S)-5-amino-6-(3,5-difluorobenzyloxy)-4-hydroxy-2-methylhexanoic acid ((S)-1-benzylcarbamoyl-2-methylpropyl)amide (1067648-45-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / -15 - 0 °C

1.2: 0 - 20 °C

2.1: 2-hydroxypyridin; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 96 h / Reflux

3.1: water; triphenylphosphine / methanol / 20 °C

With 2-hydroxypyridin; di-isopropyl azodicarboxylate; water; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol;

DOI:10.1016/j.ejmech.2009.11.013

Reference yield:

5,6-di-O-benzyl-2,3-dideoxy-2-methyl-D-glucono-1,4-lactone (1067648-40-1) → (2R,4S,5S)-5-amino-6-(3,5-difluorobenzyloxy)-4-hydroxy-2-methylhexanoic acid ((S)-1-benzylcarbamoyl-2-methylpropyl)amide (1067648-45-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: palladium on activated charcoal; hydrogen / ethanol

2.1: di(n-butyl)tin oxide / toluene / 5 h / Reflux

2.2: 90 °C

3.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / -15 - 0 °C

3.2: 0 - 20 °C

4.1: 2-hydroxypyridin; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 96 h / Reflux

5.1: water; triphenylphosphine / methanol / 20 °C

With 2-hydroxypyridin; di-isopropyl azodicarboxylate; palladium on activated charcoal; water; hydrogen; di(n-butyl)tin oxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; ethanol; toluene;

DOI:10.1016/j.ejmech.2009.11.013

upstream raw materials:

2,3-dideoxy-2-methyl-D-glucono-1,4-lactone

methyl 5,6-di-O-benzyl-2,3-dideoxy-D-glucofuranoside

2,3-dideoxy-6-O-(3,5-difluorobenzyl)-2-methyl-D-glucono-1,4-lactone

5,6-di-O-benzyl-2,3-dideoxy-D-glucono-1,4-lactone

Downstream raw materials:

(1R,2R,4S)-4-(methanesulphonyl(methyl)amino)-cyclopentane-1,2-dicarboxylic acid 1-{[(1S,2S,4R)-4-((S)-1-benzylcarbamoyl-2-methyl-propylcarbamoyl)-1-(3,5-difluoro-benzyloxymethyl)-2-hydroxy-pentyl]-amide} 2-[((R)-1-phenyl-ethyl)-amide]

((S)-1-[(S)-1-[(1S,2S,4R)-4-((S)-1-benzylcarbamoyl-2-methylpropylcarbamoyl)-1-(3,5-difluorobenzyloxymethyl)-2-hydroxypentylcarbamoyl]-3-methylsulfanylpropylcarbamoyl]-2-methylpropyl)carbamic acid tert-butyl ester

N-[(1S,2S,4R)-4-((S)-1-benzylcarbamoyl-2-methyl-propylcarbamoyl)-1-(3,5-difluoro-benzyloxymethyl)-2-hydroxy-pentyl]-5-(methanesulphonyl(methyl)amino)-N'-methyl-isophthalamide

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