Fmoc-11-aminoundecanoic acid

Base Information

• Chemical Name: Fmoc-11-aminoundecanoic acid
• CAS No.: 88574-07-6
• Molecular Formula: C26H33 N O4
• Molecular Weight: 423.552
• Hs Code.: 2924299090
• European Community (EC) Number: 625-068-4
• DSSTox Substance ID: DTXSID20402805
• Nikkaji Number: J2.023.327C
• Wikidata: Q82206303
• Mol file: 88574-07-6.mol

Synonyms:Fmoc-11-aminoundecanoic acid;88574-07-6;Fmoc-11-Aun-OH;11-(9H-fluoren-9-ylmethoxycarbonylamino)undecanoic Acid;11-(Fmoc-amino)undecanoic acid;11-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)undecanoic acid;MFCD00235891;11-({[(9H-Fluoren-9-yl)methoxy]carbonyl}amino)undecanoic acid;N-(9-FLUORENYLMETHYLOXYCARBONYL)-11-AMINO-UNDECANOIC ACID;Undecanoic acid,11-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-;Fmoc-Aund(11)-OH;SCHEMBL178758;DTXSID20402805;IMEVDILDSCXKJW-UHFFFAOYSA-N;AKOS027327505;AS-71188;BP-28250;BP-30029;SY122206;CS-0149752;Fmoc-11-Aun-OH, >=98.0% (HPLC);FT-0679725;EN300-650342;F14541;A861727;11-(9-Fluorenylmethoxycarbonylamino)undecanoic acid;11-(9H-Fluorene-9-ylmethoxycarbonylamino)undecanoic acid;BENZYL4,6-O-BENZYLIDENE-ALPHA-D-MANNOPYRANOSIDE;11-(9H-fluoren-9-ylmethoxycarbonylamino)-undecanoic acid;11-(((9H-fluoren-9-yl)methoxy)carbonylamino)undecanoic acid;11-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino]undecanoic acid

Chemical Property of Fmoc-11-aminoundecanoic acid

Chemical Property:

• PSA: 75.63000
• LogP: 6.51150
• Storage Temp.: 2-8°C
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 14
• Exact Mass: 423.24095853
• Heavy Atom Count: 31
• Complexity: 530

Purity/Quality:

98%,99%, ^*data from raw suppliers

Fmoc-11-aminoundecanoicacid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NCCCCCCCCCCC(=O)O
• Description: Fmoc-11-aminoundecanoic acid can be used as a PROTAC linker in the synthesis of PROTACs and other conjugation applicaitons. Fmoc-11-aminoundecanoic acid is an alkane chian with terminal Fmoc-protected amine and carboxylic acid groups. The Fmoc group can be deprotected under basic condition to obtain the free amine which can be used for further conjugations. The terminal carboxylic acid can react with primary amine groups in the presence of activators (e.g. EDC, or HATU) to form a stable amide bond.

Technology Process of Fmoc-11-aminoundecanoic acid

There total 3 articles about Fmoc-11-aminoundecanoic 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: 92.0%

11-aminoundecanoic acid (2432-99-7,25587-80-8,84029-94-7) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → 11-(9-fluorenylmethyloxycarbonylamino)undecanoic acid (88574-07-6)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; for 24h; Heating;

DOI:10.1021/jm980495r

Reference yield: 88.0%

benzyl 11-(9-fluorenylmethyloxycarbonylamino)undecanoate (191281-06-8) → 11-(9-fluorenylmethyloxycarbonylamino)undecanoic acid (88574-07-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1016/S0040-4020(97)00397-9

Reference yield: 34.0%

11-aminoundecanoic acid (2432-99-7,25587-80-8,84029-94-7) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → 11-(9-fluorenylmethyloxycarbonylamino)undecanoic acid (88574-07-6)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; for 16h; Ambient temperature;

DOI:10.1515/znb-1983-0820

upstream raw materials:

11-aminoundecanoic acid

(fluorenylmethoxy)carbonyl chloride

benzyl 11-(9-fluorenylmethyloxycarbonylamino)undecanoate

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

Downstream raw materials:

C₅₅H₈₈N₆O₁₂

(10-{3'-[5-(tert-butoxycarbonylamino-imino-methyl)-2-methylsulfanyl-thiophene-3-sulfonyl]-6-methyl-biphenyl-2-ylcarbamoyl}-decyl)-carbamic acid 9H-fluoren-9-ylmethyl ester

Refernces

• 1、 Galoppini, Claudia,Meini, Stefania,Tancredi, Mariella,Di Fenza, Armida,Triolo, Antonio,Quartara, Laura,Maggi, Carlo A.,Formaggio, Fernando,Toniolo, Claudio,Mazzucco, Silvia,Papini, Annamaria,Rovero, Paolo. "A new class of pseudopeptide antagonists of the kinin B1 receptor containing alkyl spacers". . p. 409 - 414. Retrieved 2007/10/03.
• 2、 Boumrah, Deradji,Campbell, Malcolm M.,Fenner, Simon,Kinsman, Richard G.. "Spacer molecules in peptide sequences: Incorporation into analogues of atrial natriuretic factor". . p. 7735 - 7738. Retrieved 2007/10/02.