a-(Fmoc-amino)-cyclopropaneacetic acid

Base Information

• Chemical Name: a-(Fmoc-amino)-cyclopropaneacetic acid
• CAS No.: 1332765-55-5
• Molecular Formula: C₂₀H₁₉NO₄
• Molecular Weight: 337.375
• European Community (EC) Number: 847-213-2
• Nikkaji Number: J1.149.871J
• Mol file: 1332765-55-5.mol

Synonyms:1332765-55-5;a-(Fmoc-amino)-cyclopropaneacetic acid;2-cyclopropyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)acetic acid;(R)-Fmoc-cyclopropylglycine;(S)-Fmoc-cyclopropylglycine;MFCD06659145;SCHEMBL178793;MFCD01861824;a-(Fmoc-amino)-cyclopropaneaceticacid;AKOS012614339;SB31789;SB39954;alpha-(Fmoc-amino)cyclopropaneacetic acid;AC-30476;BS-44968;SY254075;CS-0196686;EN300-81456;F20908;Fmoc-Cyclopropylglycine (Fmoc-DL-Gly(cPr)-OH);Z1123720114;N-(9H-Fluorene-9-ylmethoxycarbonyl)-2-cyclopropylglycine;2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-cyclopropylacetic acid;2-cyclopropyl-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)acetic acid

Chemical Property of a-(Fmoc-amino)-cyclopropaneacetic acid

Chemical Property:

• Storage Temp.: 2-8°C
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 337.13140809
• Heavy Atom Count: 25
• Complexity: 496

Purity/Quality:

98.5% ^*data from raw suppliers

A-(Fmoc-Amino)-cyclopropaneaceticAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC1C(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Technology Process of a-(Fmoc-amino)-cyclopropaneacetic acid

There total 2 articles about a-(Fmoc-amino)-cyclopropaneacetic 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: 84.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + (S)-2-amino-2-cyclopropylacetic acid (49606-99-7,5687-71-8,15785-26-9,49607-01-4) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-cyclopropylacetic acid (1212257-18-5,1332765-55-5,923012-40-2)

Guidance literature:

(S)-2-amino-2-cyclopropylacetic acid; With sodium carbonate; In water; Inert atmosphere;

(fluorenylmethoxy)carbonyl chloride; In 1,4-dioxane; water; for 8h; Inert atmosphere;

DOI:10.1021/jacs.5b12557

Reference yield:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (S)-2-amino-2-cyclopropylacetic acid (49606-99-7,5687-71-8,15785-26-9,49607-01-4) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-cyclopropylacetic acid (1212257-18-5,1332765-55-5,923012-40-2)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 20 ℃; for 18h;

DOI:10.1002/anie.202017086

Reference yield:

(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-cyclopropylacetic acid (1212257-18-5,1332765-55-5,923012-40-2) + C45H76N4O14 → C65H93N5O17

Guidance literature:

(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-cyclopropylacetic acid; With 1-hydroxy-7-aza-benzotriazole; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; at 20 ℃; for 1h;

C₄₅H₇₆N₄O₁₄; In dichloromethane; at 20 ℃; for 20h;

DOI:10.1021/acs.jmedchem.1c00327

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

(S)-2-amino-2-cyclopropylacetic acid

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

Refernces

• 1、 Nicolaou,Yin, Jun,Mandal, Debashis,Erande, Rohan D.,Klahn, Philipp,Jin, Michael,Aujay, Monette,Sandoval, Joseph,Gavrilyuk, Julia,Vourloumis, Dionisios. "Total Synthesis and Biological Evaluation of Natural and Designed Tubulysins". supporting information. p. 1698 - 1708. Retrieved 2016/02/20.