(2S,4R)-4-methyl-N-(9-(9-phenylfluorenyl))proline tert-butyl ester

Base Information

• Chemical Name: (2S,4R)-4-methyl-N-(9-(9-phenylfluorenyl))proline tert-butyl ester
• CAS No.: 119595-87-8
• Molecular Formula: C₂₉H₃₁NO₂
• Molecular Weight: 425.571
• Mol file: 119595-87-8.mol

Synonyms:(2S,4R)-4-methyl-N-(9-(9-phenylfluorenyl))proline tert-butyl ester

Chemical Property of (2S,4R)-4-methyl-N-(9-(9-phenylfluorenyl))proline tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-4-methyl-N-(9-(9-phenylfluorenyl))proline tert-butyl ester

There total 6 articles about (2S,4R)-4-methyl-N-(9-(9-phenylfluorenyl))proline tert-butyl ester 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: 89.0%

α-tert-butyl (2S,4R)-5-hydroxy-4-methyl-2-N-(9-(9-phenylfluorenyl)amino)pentanoate (119595-81-2) → (2S,4R)-4-methyl-N-(9-(9-phenylfluorenyl))proline tert-butyl ester (119595-87-8)

Guidance literature:

With carbon tetrabromide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; for 1h; Ambient temperature;

DOI:10.1021/jo00269a022

Reference yield:

<2S,4(R,S)>-α-tert-butyl γ-methyl N-(9-(9-phenylfluorenyl))-4-methylglutamate (119595-74-3,119595-77-6) → (2S,4R)-4-methyl-N-(9-(9-phenylfluorenyl))proline tert-butyl ester (119595-87-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 21 percent

2: 86 percent

1: Elimination / 2: Cyclization;

DOI:10.1016/S0040-4020(00)00764-X

Reference yield:

L-glutamic acid 5-methyl ester (1499-55-4) → (2S,4R)-4-methyl-N-(9-(9-phenylfluorenyl))proline tert-butyl ester (119595-87-8)

Guidance literature:

Multi-step reaction with 6 steps

1: CHCl₃ / 2 h / Heating

2: lead nitrate, Et₃N / CHCl₃ / 87 h / Ambient temperature

3: 75 percent / CH₂Cl₂ / 16 h / Ambient temperature

4: 1.) potassium hexamethyldisilazide (KHMDS) / 1.) THF, toluene, -78 deg C, 1 h, 2.) THF, toluene, 3 h

5: 66 percent / LiAlH₄ / tetrahydrofuran / 4 h / -78 °C

6: 89 percent / PPh₃, CBr₄, iPr₂NEt / tetrahydrofuran / 1 h / Ambient temperature

With lithium aluminium tetrahydride; lead(II) nitrate; carbon tetrabromide; potassium hexamethylsilazane; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; chloroform;

DOI:10.1021/jo00269a022

upstream raw materials:

α-tert-butyl (2S,4R)-5-hydroxy-4-methyl-2-N-(9-(9-phenylfluorenyl)amino)pentanoate

<2S,4(R,S)>-α-tert-butyl γ-methyl N-(9-(9-phenylfluorenyl))-4-methylglutamate

L-glutamic acid 5-methyl ester

L-N-(9-(9-phenylfluorenyl))glutamic acid γ-methylester

Downstream raw materials:

trans-4-methyl-L-proline