Fmoc-3-(1-naphthyl)-L-alanine

Base Information

• Chemical Name: Fmoc-3-(1-naphthyl)-L-alanine
• CAS No.: 96402-49-2
• Molecular Formula: C28H23NO4
• Molecular Weight: 437.495
• Hs Code.: 29242990
• European Community (EC) Number: 692-640-8
• DSSTox Substance ID: DTXSID70370323
• Wikidata: Q72478719
• Mol file: 96402-49-2.mol

Synonyms:96402-49-2;Fmoc-1-Nal-OH;Fmoc-3-(1-naphthyl)-L-alanine;Fmoc-beta-(1-naphthyl)-L-alanine;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-naphthalen-1-ylpropanoic acid;(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(naphthalen-1-yl)propanoic acid;MFCD00151914;(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(naphthalen-1-yl)propanoic acid;SCHEMBL800112;FMOC-ALA(1-NAPH)-OH;DTXSID70370323;Fmoc-1-Nal-OH, >=98.0%;AKOS015837327;AC-9933;AM83700;CS-W011611;DS-2411;HY-W010895;Fmoc-L-1-naphthylalanine (Fmoc-L-1Nal-OH);EN300-650655;Z1741982769;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(1-naphthyl)propanoate;(S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-3-(NAPHTHALEN-1-YL)PROPANOIC ACID

Chemical Property of Fmoc-3-(1-naphthyl)-L-alanine

Chemical Property:

• Appearance/Colour: white to beige powder
• Vapor Pressure: 4.95E-20mmHg at 25°C
• Melting Point: 171-183℃
• Refractive Index: 1.6290 (estimate)
• Boiling Point: 690.7 °C at 760 mmHg
• PKA: 3.77±0.30(Predicted)
• Flash Point: 371.6 °C
• PSA: 75.63000
• Density: 1.296 g/cm³
• LogP: 5.76510
• Storage Temp.: 2-8°C
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 437.16270821
• Heavy Atom Count: 33
• Complexity: 673

Purity/Quality:

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

Fmoc-1-Nal-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC=C2CC(C(=O)O)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35
• Isomeric SMILES: C1=CC=C2C(=C1)C=CC=C2C[C@@H](C(=O)O)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35
• Uses: Fmoc-1-Nal-OH, is an amino acid derivative used in chemical synthesis and peptide chemistry.

Technology Process of Fmoc-3-(1-naphthyl)-L-alanine

There total 1 articles about Fmoc-3-(1-naphthyl)-L-alanine 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:

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + L-1-naphthylalanine (55516-54-6,68798-79-8,7758-42-1) → Nα-Fmoc-3-(1'-naphthyl)alanine (96402-49-2,138774-93-3)

Guidance literature:

With sodium carbonate;

DOI:10.1021/jm00053a001

Reference yield: 29.6%

Fmoc-Lys(ivDde)-Wang resin + 4-[(9H-fluoren-9-ylmethoxycarbonylamino)methyl]cyclohexanecarboxylic acid + Nα-Fmoc-3-(1'-naphthyl)alanine (96402-49-2,138774-93-3) + 1,4,7-tris(tert-butoxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane-10-acetic acid (137076-54-1) + 2-isocyanato-hexanedioic acid di-tert-butyl ester → C50H73N9O16

Guidance literature:

Fmoc-Lys(ivDde)-Wang resin; With piperidine; In N,N-dimethyl-formamide; Wang resin

2-isocyanato-hexanedioic acid di-tert-butyl ester; With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 16h; Wang resin

4-[(9H-fluoren-9-ylmethoxycarbonylamino)methyl]cyclohexanecarboxylic acid; N^α-Fmoc-3-(1'-naphthyl)alanine; 1,4,7-tris(tert-butoxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane-10-acetic acid; Further stages;

Reference yield: 21.0%

5-azidovaleric acid (79583-98-5) + N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Leu-OH (35661-60-0) + (S)-2-{[((9H-fluoren-9-yl)methoxy)carbonyl]amino}-3-(prop-2-yn-1-yloxy)propanoic acid (1354752-75-2) + Nα-Fmoc-3-(1'-naphthyl)alanine (96402-49-2,138774-93-3) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-α-aminoisobutyric acid (94744-50-0) → C36H49N9O7

Guidance literature:

Fmoc-Leu-OH; With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20 ℃; for 0.05h;

With piperidine; In N,N-dimethyl-formamide; for 0.0166667h;

5-azidovaleric acid; N-(fluoren-9-ylmethoxycarbonyl)glycine; (S)-2-{[((9H-fluoren-9-yl)methoxy)carbonyl]amino}-3-(prop-2-yn-1-yloxy)propanoic acid; N^α-Fmoc-3-(1'-naphthyl)alanine; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-α-aminoisobutyric acid; Further stages;

DOI:10.1021/acs.jmedchem.1c01334

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

L-1-naphthylalanine

Downstream raw materials:

c[Asu-Nal-β3Tyr-Arg]; Asu = (S)-2-aminosuberic acid; Nal = 1-naphthylalanine

Refernces