(S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid

Base Information

• Chemical Name: (S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid
• CAS No.: 1246651-90-0
• Molecular Formula: C₂₄H₂₇NO₆
• Molecular Weight: 425.481
• Mol file: 1246651-90-0.mol

Synonyms:(S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid

Chemical Property of (S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid

Chemical Property:

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

Purity/Quality:

97% ^*data from raw suppliers

(S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic Acid is used as a reactant in the synthesis of β/α-chimeric peptides, of DPA-β-decapeptide and of PEGylated β-heptapeptide.

Technology Process of (S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid

There total 8 articles about (S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic 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: 94.0%

C9H17NO4 (83049-33-6) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → (S)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid (1246651-90-0)

Guidance literature:

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

DOI:10.1002/adsc.200800053

Reference yield: 80.0%

tert-butyl 3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-diazo-4-oxopentanoate (244031-63-8) → (9H-fluoren-9-yl)methyl (R)-1-(hydroxycarbonyl)-3-(tert-butoxycarbonyl)propan-2-ylcarbamate (209252-17-5,1246651-90-0)

Guidance literature:

With silver benzoate; In 1,4-dioxane; water; at 70 ℃; for 5h;

Reference yield:

Fmoc-(tBu)Asp-OH (71989-14-5) → (9H-fluoren-9-yl)methyl (R)-1-(hydroxycarbonyl)-3-(tert-butoxycarbonyl)propan-2-ylcarbamate (209252-17-5,1246651-90-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / 1H-benzotriazol-1-yl-N-oxytrispyrrolidinophosphonium PF₆^(1-); N-ethyldiisopropylamine / tetrahydrofuran; dimethylformamide; diethyl ether / 0.25 h / 0 °C

2: 79 percent / silver benzoate / dioxane; H₂O / 70 °C

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; silver benzoate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; diethyl ether; water; N,N-dimethyl-formamide; 2: Wolff rearrangement;

upstream raw materials:

tert-butyl 3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-diazo-4-oxopentanoate

Fmoc-(tBu)Asp-OH

C₉H₁₇NO₄

(fluorenylmethoxy)carbonyl chloride

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