Fmoc-L-norvaline

Base Information

• Chemical Name: Fmoc-L-norvaline
• CAS No.: 135112-28-6
• Molecular Formula: C20H21NO4
• Molecular Weight: 339.391
• Hs Code.: 29242990
• DSSTox Substance ID: DTXSID80426880
• Nikkaji Number: J1.684.310E
• Wikidata: Q72478747
• Mol file: 135112-28-6.mol

Synonyms:Fmoc-Nva-OH;Fmoc-L-norvaline;135112-28-6;N-Fmoc-L-norvaline;N-(9-Fluorenylmethyloxycarbonyl)-L-Norvaline;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic acid;MFCD00155631;L-Norvaline, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-;Fmoc-Nva-OH Fmoc-L-norvaline;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)pentanoic acid;(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)pentanoic acid;Fmoc-L-2-aminovaleric acid;Fmoc-norvaline;SCHEMBL120255;DTXSID80426880;JBIJSEUVWWLFGV-SFHVURJKSA-N;AKOS015910845;AM82599;CS-W013923;HY-W013207;FMOC-L-NHCH[CH3(CH2)2]-COOH;Fmoc-Nva-OH, >=98.0% (HPLC);AS-68348;PD196887;F1117;N-(9H-Fluorene-9-ylmethoxycarbonyl)norvaline;EN300-624058;M06138;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-norvaline;J-300352;Z1946056419;(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)pentanoic acid

Chemical Property of Fmoc-L-norvaline

Chemical Property:

• Appearance/Colour: White powder
• Melting Point: 151-155 °C
• Boiling Point: 557.9 °C at 760 mmHg
• PKA: 3.91±0.20(Predicted)
• Flash Point: 291.2 °C
• PSA: 75.63000
• Density: 1.23 g/cm³
• LogP: 4.16930
• Storage Temp.: 2-8°C
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 339.14705815
• Heavy Atom Count: 25
• Complexity: 458

Purity/Quality:

99% ^*data from raw suppliers

N-(9-Fluorenylmethoxycarbonyl)-L-norvaline ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: CCC[C@@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Uses: Fmoc-nva-oh is a tumor targeting Polypeptide and its application in preparation of Polypeptide drug conjugate.

Technology Process of Fmoc-L-norvaline

There total 5 articles about Fmoc-L-norvaline 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:

L-Norvaline (6600-40-4,498-18-0) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → Fmoc-norvaline-OH (135112-28-6)

Guidance literature:

L-Norvaline; With sodium carbonate; In 1,4-dioxane; water; Cooling with ice;

(fluorenylmethoxy)carbonyl chloride; In 1,4-dioxane; water; at 20 ℃; for 5h;

DOI:10.1002/bkcs.11694

Reference yield:

2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)pentanoic acid → Fmoc-norvaline-OH (135112-28-6) + (R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)pentanoic acid (144701-24-6)

Guidance literature:

With trifluoroacetic acid; In hexane; isopropyl alcohol; at 25 ℃; Reagent/catalyst; Resolution of racemate;

DOI:10.1002/bkcs.11694

Reference yield:

{1-[(E)-2-((1S,2S,5R)-2-Isopropyl-5-methyl-cyclohexyl)-vinyl]-butyl}-carbamic acid 9H-fluoren-9-ylmethyl ester → Fmoc-norvaline-OH (135112-28-6) + (R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)pentanoic acid (144701-24-6)

Guidance literature:

{1-[(E)-2-((1S,2S,5R)-2-Isopropyl-5-methyl-cyclohexyl)-vinyl]-butyl}-carbamic acid 9H-fluoren-9-ylmethyl ester; With ozone; In dichloromethane; at -78 ℃; for 0.0833333h;

With dimethylsulfide; In dichloromethane; at -78 - 20 ℃;

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; at 20 ℃; for 5h; Title compound not separated from byproducts;

DOI:10.1021/ol052034n

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

L-Norvaline

2-aminopentanoic acid

Refernces

• 1、 Gagnon, David,Lauzon, Sophie,Godbout, Cedrickx,Spino, Claude. "Sterically biased 3,3-sigmatropic rearrangement of azides: Efficient preparation of nonracemic α-amino acids and heterocycles". . p. 4769 - 4771. Retrieved 2007/10/03.