FMoc-α-Me-Asp(OtBu)-OH

Base Information

• Chemical Name: FMoc-α-Me-Asp(OtBu)-OH
• CAS No.: 1072845-47-6
• Molecular Formula: C₂₄H₂₇NO₆
• Molecular Weight: 425.481
• Mol file: 1072845-47-6.mol

Synonyms:Fmoc-alpha-Me-L-Asp(tBu)-OH

Chemical Property of FMoc-α-Me-Asp(OtBu)-OH

Chemical Property:

• PSA: 101.93000
• LogP: 4.49110
• Storage Temp.: 2-8°C

Purity/Quality:

99.3% ^*data from raw suppliers

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-2-methyl-4-oxobutanoicacid 95+% ^*data from reagent suppliers

Safty Information:

• Statements: 22-38-40-48/20/22
• Safety Statements: 36/37

MSDS Files:

Useful:

Technology Process of FMoc-α-Me-Asp(OtBu)-OH

There total 2 articles about FMoc-α-Me-Asp(OtBu)-OH 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: 85.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + O4-(tert-butyl) hydrogen (S)-2-methylaspartate (147108-45-0,1231709-25-3,1217977-71-3) → (S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methyl-succinic acid 4-tert-butyl ester (1072845-47-6)

Guidance literature:

O⁴-(tert-butyl) hydrogen (S)-2-methylaspartate; With sodium carbonate; In 1,4-dioxane; water; at 20 ℃; for 0.166667h;

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide; In 1,4-dioxane; water; at 20 ℃; for 12h;

DOI:10.1016/j.tet.2018.07.029

Reference yield:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + O4-(tert-butyl) hydrogen (R)-2-methylaspartate (147108-45-0,1231709-25-3,1217977-71-3) → (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-tert-butoxy-2-methyl-4-oxobutanoic acid (1231709-26-4,1072845-47-6)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 20 ℃; Cooling with ice;

DOI:10.1021/jm800487r

Reference yield:

(S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methyl-succinic acid 4-tert-butyl ester (1072845-47-6) → tert-butyl (3S)-4-hydroxy-3-methyl-3-(2-(3-methyl-2,6-dioxo-5-(4-(quinoxalin-2-ylamino)benzamido)-3,6-dihydropyrimidin-1(2H)-yl)propanamido)butanoate

Guidance literature:

Multi-step reaction with 4 steps

1: 4-methyl-morpholine / dichloromethane / 1 h / 0 °C

2: sodium tetrahydroborate / dichloromethane / 18 h / 0 - 20 °C

3: pyrrolidine / acetonitrile / 24 h / 20 °C

4: N,N-dimethyl-formamide / 52 h / 20 - 80 °C

With pyrrolidine; 4-methyl-morpholine; sodium tetrahydroborate; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.tet.2018.07.029

upstream raw materials:

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

O⁴-(tert-butyl) hydrogen (R)-2-methylaspartate

O⁴-(tert-butyl) hydrogen (S)-2-methylaspartate

Refernces

• 1、 Long, Ya-Qiu,Xue, Ting,Song, Yan-Li,Liu, Zu-Long,Huang, Shao-Xu,Yu, Qiang. "Synthesis and utilization of chiral α-methylated α-amino acids with a carboxyalkyl side chain in the design of novel Grb2-SH2 peptide inhibitors free of phosphotyrosine". experimental part. p. 6371 - 6380. Retrieved 2009/10/17.