(2R,3S)-2-[Benzyl-(9-phenyl-9H-fluoren-9-yl)-amino]-3-methyl-succinic acid 1-methyl ester

Base Information

• Chemical Name: (2R,3S)-2-[Benzyl-(9-phenyl-9H-fluoren-9-yl)-amino]-3-methyl-succinic acid 1-methyl ester
• CAS No.: 184353-93-3
• Molecular Formula: C₃₂H₂₉NO₄
• Molecular Weight: 491.587
• Mol file: 184353-93-3.mol

Synonyms:(2R,3S)-2-[Benzyl-(9-phenyl-9H-fluoren-9-yl)-amino]-3-methyl-succinic acid 1-methyl ester

Chemical Property of (2R,3S)-2-[Benzyl-(9-phenyl-9H-fluoren-9-yl)-amino]-3-methyl-succinic acid 1-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-2-[Benzyl-(9-phenyl-9H-fluoren-9-yl)-amino]-3-methyl-succinic acid 1-methyl ester

There total 1 articles about (2R,3S)-2-[Benzyl-(9-phenyl-9H-fluoren-9-yl)-amino]-3-methyl-succinic acid 1-methyl 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: 29.0%

Dimethyl D-(3S)-N-(9-phenylfluoren-9-yl)-N-benzyl-3-methylaspartate (155069-77-5) → (2R,3S)-2-[Benzyl-(9-phenyl-9H-fluoren-9-yl)-amino]-3-methyl-succinic acid 1-methyl ester (184353-93-3) + (2R,3R)-2-[Benzyl-(9-phenyl-9H-fluoren-9-yl)-amino]-3-methyl-succinic acid 1-methyl ester

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; at 60 ℃; for 24h;

DOI:10.1021/ja961683e

Reference yield: 96.0%

tert-butyl L-alaninate hydrochloride (13404-22-3) + (2R,3S)-2-[Benzyl-(9-phenyl-9H-fluoren-9-yl)-amino]-3-methyl-succinic acid 1-methyl ester (184353-93-3) → D-erythro-N-(9-phenylfluoren-9-yl)-N-benzyl-β-Me-iso-Asp(OMe)-L-Ala-OtBu (225780-70-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; 1.) 0 deg C, 3 h, 2.) room temperature, 12 h;

DOI:10.1016/S0968-0896(98)00254-5

Reference yield:

(2R,3S)-2-[Benzyl-(9-phenyl-9H-fluoren-9-yl)-amino]-3-methyl-succinic acid 1-methyl ester (184353-93-3) → Microcystin-LA (96180-79-9)

Guidance literature:

Multi-step reaction with 12 steps

1: TFA, H₂ / 10percent Pd/C / ethyl acetate; CH₂Cl₂ / 14 h / 2585.7 Torr

2: aq. Na₂CO₃ / dioxane / 25 h / Ambient temperature

3: 88 percent / DIEA, HATU / dimethylformamide / 9 h / Ambient temperature

4: TFA / 0.5 h

5: collidine, HATU / dimethylformamide / a) 0 deg C, 1 h, b) RT, 19 h

6: TFA / 0.5 h

7: collidine, HATU / dimethylformamide / a) 0 deg C, 1 h, b) RT, 14 h

8: 84 percent / Zn, HOAc / 4 h

9: 83 percent / DCC / ethyl acetate / a) 0 deg C, 2 h, b) RT, 22 h

10: TFA / 0.83 h

11: phosphate buffer, pH 9.5 / CHCl₃ / 1 h

12: 50 percent / 0.1 M aq. LiOH / tetrahydrofuran / 5 h / 0 °C

With 2,3,5-trimethyl-pyridine; lithium hydroxide; phosphate buffer; hydrogen; sodium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; zinc; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ja961683e

upstream raw materials:

Dimethyl D-(3S)-N-(9-phenylfluoren-9-yl)-N-benzyl-3-methylaspartate

Downstream raw materials:

D-erythro-N-(9-phenylfluoren-9-yl)-N-benzyl-β-Me-iso-Asp(OMe)-L-Ala-OtBu

Boc-D-iso-Glu(OMe)-N-(cyclohexyl)-Gly-D-Ala-L-Leu-D-β-Me-iso-Asp(OMe)-L-Ala-OtBu

Boc-D-iso-Glu(OMe)-MeΔAla-D-Ala-3-cyclohexyl-L-Ala-D-β-Me-iso-Asp(OMe)-L-Ala-OtBu

cyclo