(R)-Fmoc-beta2-homoleucine

Base Information

• Chemical Name: (R)-Fmoc-beta2-homoleucine
• CAS No.: 1018899-99-4
• Molecular Formula: C₂₂H₂₅NO₄
• Molecular Weight: 367.445
• Hs Code.: 2924299090
• Mol file: 1018899-99-4.mol

Synonyms:(2R)-2-[(9H-fluoren-9-ylmethoxycarbonylamino)methyl]-4-methylpentanoic acid;

Chemical Property of (R)-Fmoc-beta2-homoleucine

Chemical Property:

• Melting Point: 134-135 °C
• Boiling Point: 572.1±33.0 °C(Predicted)
• PKA: 4.45±0.21(Predicted)
• PSA: 79.12000
• Density: 1.188±0.06 g/cm3(Predicted)
• LogP: 4.47640
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

(R)-Fmoc-beta2-homoleucine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (R)-Fmoc-beta2-homoleucine

There total 13 articles about (R)-Fmoc-beta2-homoleucine 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: 46.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (2R)-([amino]methyl)-4-methylpentanoic acid (210345-89-4) → (2R)-2-({[(9H-fluoren-9-ylmethoxy)carbonyl]amino}methyl)-4-methylpentanoic acid (1018899-99-4)

Guidance literature:

With sodium carbonate; In water; acetone; at 20 ℃; for 20h; enantioselective reaction;

DOI:10.1016/j.tetasy.2008.12.023

Reference yield:

benzyl 4-methyl-2-methylenepentanoate (118053-31-9) → (2R)-2-({[(9H-fluoren-9-ylmethoxy)carbonyl]amino}methyl)-4-methylpentanoic acid (1018899-99-4)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / dimethylformamide / 24 h / 20 °C

2: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

3: HCOONH₄ / 10percent Pd/C / methanol / 60 °C

4: NaHCO₃ / tetrahydrofuran; H₂O / 0 - 20 °C

With ammonium formate; sodium hydrogencarbonate; triethylamine; lithium hexamethyldisilazane; 10percent Pd/C; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; 1: Michael addition;

DOI:10.1021/jo026738b

Reference yield:

2-acetyl-4-methyl-pentanoic acid benzyl ester (501330-86-5) → (2R)-2-({[(9H-fluoren-9-ylmethoxy)carbonyl]amino}methyl)-4-methylpentanoic acid (1018899-99-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / LiHMDS / tetrahydrofuran / 6 h / 20 °C

2: triethylamine / dimethylformamide / 24 h / 20 °C

3: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

4: HCOONH₄ / 10percent Pd/C / methanol / 60 °C

5: NaHCO₃ / tetrahydrofuran; H₂O / 0 - 20 °C

With ammonium formate; sodium hydrogencarbonate; triethylamine; lithium hexamethyldisilazane; 10percent Pd/C; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; 2: Michael addition;

DOI:10.1021/jo026738b

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

(2R)-([amino]methyl)-4-methylpentanoic acid

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

benzyl 4-methyl-2-methylenepentanoate