(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpent-4-enoic acid

Base Information

• Chemical Name: (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpent-4-enoic acid
• CAS No.: 288617-76-5
• Molecular Formula: C21H21NO4
• Molecular Weight: 351.40
• Hs Code.: 2924299090
• European Community (EC) Number: 803-594-7
• Nikkaji Number: J1.366.547H
• Mol file: 288617-76-5.mol

Synonyms:288617-76-5;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpent-4-enoic acid;Fmoc-alpha-allyl-D-Ala;(R)-N-Fmoc-2-(2'-propylenyl)alanine;(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methylpent-4-enoic acid;(R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-methylpent-4-enoic acid;FMOC-ALPHA-METHYL-D-ALLYLGLYCINE;Fmoc-(R)-2-amino-2-methyl-4-pentenoic acid;4-Pentenoic acid, 2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-2-methyl-, (2R)-;Fmoc-D-(Me)Gly(Allyl)-OH;SCHEMBL15004648;MFCD08063323;AKOS015837079;AM10145;CS-W005913;DS-7949;HY-W005913;AC-27569;PD196453;F12307;Fmoc-|A inverted exclamation mark-allyl-D-Ala;A851330;S-288617-76-5;Fmoc-alpha-methyl-D-Allylglycine (Fmoc-D-aMeGly(Allyl)-OH);(2R)-2-(9H-Fluorene-9-ylmethoxycarbonylamino)-2-methyl-4-pentenoic acid;(R)-2-(((9H-fluoren-9-yl)methoxy)carbonyl)-2-methylpent-4-enoic acid;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpent-4-enoicacid

Chemical Property of (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpent-4-enoic acid

Chemical Property:

• Boiling Point: 564.259 °C at 760 mmHg
• PKA: 3.81±0.11(Predicted)
• Flash Point: 295.054 °C
• PSA: 75.63000
• Density: 1.224 g/cm³
• LogP: 4.33540
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 351.14705815
• Heavy Atom Count: 26
• Complexity: 526

Purity/Quality:

98%Min ^*data from raw suppliers

Fmoc-alpha-methyl-D-allylglycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC=C)(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: C[C@@](CC=C)(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Technology Process of (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpent-4-enoic acid

There total 7 articles about (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpent-4-enoic 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: 80.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + Cα-methyl-D-allylglycine (96886-56-5) → (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpent-4-enoic acid (288617-71-0,288617-76-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; water; at 20 ℃;

DOI:10.1021/acs.jmedchem.6b01796

Reference yield:

2-(tert-butoxycarbonylmethyl-amino)-2-methyl-pent-4-enoic acid + 9-fluorenylmethyl carbamate (84418-43-9) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpent-4-enoic acid (288617-71-0,288617-76-5)

Guidance literature:

2-(tert-butoxycarbonylmethyl-amino)-2-methyl-pent-4-enoic acid; In dichloromethane; trifluoroacetic acid; at 0 ℃; for 0.5h;

9-fluorenylmethyl carbamate; With sodium carbonate; In water; acetone; at 20 ℃; for 12h; Further stages.;

DOI:10.1021/ja000563a

Reference yield:

2-(tert-butoxycarbonylmethyl-amino)-2-methyl-pent-4-enoic acid + 9-fluorenylmethyl carbamate (84418-43-9) → (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpent-4-enoic acid (288617-71-0,288617-76-5)

Guidance literature:

2-(tert-butoxycarbonylmethyl-amino)-2-methyl-pent-4-enoic acid; In dichloromethane; trifluoroacetic acid; at 0 ℃; for 0.5h;

9-fluorenylmethyl carbamate; With sodium carbonate; In water; acetone; at 20 ℃; for 12h; Further stages.;

DOI:10.1021/ja000563a

upstream raw materials:

9-fluorenylmethyl carbamate

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

(S)-α-allylalanine

C^α-methyl-D-allylglycine

Downstream raw materials:

C₇₄H₁₁₀N₁₈O₁₄

Refernces

• 1、 Karatas, Hacer,Li, Yangbing,Liu, Liu,Ji, Jiao,Lee, Shirley,Chen, Yong,Yang, Jiuling,Huang, Liyue,Bernard, Denzil,Xu, Jing,Townsend, Elizabeth C.,Cao, Fang,Ran, Xu,Li, Xiaoqin,Wen, Bo,Sun, Duxin,Stuckey, Jeanne A,Lei, Ming,Dou, Yali,Wang, Shaomeng. "Discovery of a Highly Potent, Cell-Permeable Macrocyclic Peptidomimetic (MM-589) Targeting the WD Repeat Domain 5 Protein (WDR5)-Mixed Lineage Leukemia (MLL) Protein-Protein Interaction". . p. 4818 - 4839. Retrieved 2017/06/28.
• 2、 Long, Ya-Qiu,Huang, Shao-Xu,Zawahir, Zahrah,Xu, Zhong-Liang,Li, Huiyuan,Sanchez, Tino W.,Zhi, Ying,De Houwer, Stephanie,Christ, Frauke,Debyser, Zeger,Neamati, Nouri. "Design of cell-permeable stapled peptides as HIV-1 integrase inhibitors". . p. 5601 - 5612. Retrieved 2013/07/26.