(2S,3S,4R)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-2-methyl-5-(2'-methylphenyl)pentanoic acid

Base Information

• Chemical Name: (2S,3S,4R)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-2-methyl-5-(2'-methylphenyl)pentanoic acid
• CAS No.: 1315271-32-9
• Molecular Formula: C₂₈H₂₉NO₅
• Molecular Weight: 459.542

Synonyms:(2S,3S,4R)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-2-methyl-5-(2'-methylphenyl)pentanoic acid

Chemical Property of (2S,3S,4R)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-2-methyl-5-(2'-methylphenyl)pentanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (2S,3S,4R)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-2-methyl-5-(2'-methylphenyl)pentanoic acid

There total 6 articles about (2S,3S,4R)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-2-methyl-5-(2'-methylphenyl)pentanoic 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:

C13H19NO3 + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → (2S,3S,4R)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-2-methyl-5-(2'-methylphenyl)pentanoic acid (1315271-32-9)

Guidance literature:

With potassium carbonate; In 1,4-dioxane; water; at 20 ℃;

DOI:10.1016/j.bmc.2011.04.047

Reference yield:

N-(t-butoxycarbonyl)-D-2-methylphenylalaninal (1315271-13-6) → (2S,3S,4R)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-2-methyl-5-(2'-methylphenyl)pentanoic acid (1315271-32-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / -78 - 0 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

1.3: 4 h / 0 °C

2.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 3 h / 0 °C

2.2: pH Ca_. 2

3.1: dimethylsulfide; trifluoroacetic acid / 2 h / 20 °C / Inert atmosphere

4.1: potassium carbonate / 1,4-dioxane; water / 20 °C

With dimethylsulfide; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; potassium carbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;

DOI:10.1016/j.bmc.2011.04.047

Reference yield:

N-(t-butoxycarbonyl)-D-2-methylphenylalanine N-methyl-N-methoxyamide (923563-62-6) → (2S,3S,4R)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-2-methyl-5-(2'-methylphenyl)pentanoic acid (1315271-32-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere

2.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / -78 - 0 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

2.3: 4 h / 0 °C

3.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 3 h / 0 °C

3.2: pH Ca_. 2

4.1: dimethylsulfide; trifluoroacetic acid / 2 h / 20 °C / Inert atmosphere

5.1: potassium carbonate / 1,4-dioxane; water / 20 °C

With lithium aluminium tetrahydride; dimethylsulfide; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; potassium carbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;

DOI:10.1016/j.bmc.2011.04.047

upstream raw materials:

N-(t-butoxycarbonyl)-D-2-methylphenylalanine N-methyl-N-methoxyamide

N-(t-butoxycarbonyl)-D-2-methylphenylalaninal

(1R,2S,3S,4'S)-[2-hydroxy-1-(2'-methylbenzyl)-4-(4'-isopropyl-2'-oxo-oxazolidin-3'-yl)-3-methyl-4-oxobutyl]carbamic acid tert-butyl ester

(2S,3S,4R)-4-tert-butoxycarbonylamino-3-hydroxy-2-methyl-5-(2'-methylphenyl)pentanoic acid

Downstream raw materials:

C₅₄H₈₁N₁₉O₉S₂

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