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

Base Information

• Chemical Name: Fmoc-3-(1-naphthyl)-D-alanine
• CAS No.: 138774-93-3
• Molecular Formula: C₂₈H₂₃NO₄
• Molecular Weight: 437.495
• Hs Code.: 29242990
• DSSTox Substance ID: DTXSID10427845
• Wikidata: Q72478721
• Mol file: 138774-93-3.mol

Synonyms:138774-93-3;Fmoc-3-(1-naphthyl)-D-alanine;Fmoc-D-1-Nal-OH;Fmoc-D-1-Naphthylalanine;(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-naphthalen-1-ylpropanoic acid;Fmoc-beta-(1-naphthyl)-D-alanine;SCHEMBL3725027;FMOC-D-ALA(1-NAPH)-OH;DTXSID10427845;MFCD00191200;FMOC-3-(1-NAPHTHYL)-D-ALA;AKOS015837412;AKOS015896044;AC-9934;AM83699;CS-W014451;HY-W013735;(R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(naphthalen-1-yl)propanoic acid;(R)-2-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-3-NAPHTHALEN-1-YL-PROPIONIC ACID;DS-15477;Fmoc-D-1-Nal-OH, >=96.0% (HPLC);A50153;M03148;EN300-3442139;J-007173;(2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(naphthalen-1-yl)propanoic acid;(R)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-3-(NAPHTHALEN-1-YL)PROPANOIC ACID;1-Naphthalenepropanoic acid, alpha-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-, (alphaR)-

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

Chemical Property:

• Vapor Pressure: 4.95E-20mmHg at 25°C
• Refractive Index: 1.671
• 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-d-1-naphthylalanine ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

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-d-1-naphthylalanine, is an amino acid derivative used in chemical synthesis and peptide chemistry.

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

There total 2 articles about Fmoc-3-(1-naphthyl)-D-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: 85.0%

2-amino-3-(1-naphthyl)propanoic acid (28095-56-9,68798-79-8,7758-42-1) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → Nα-fluorenylmethyloxycarbonyl-DL-1-naphthylalanine (176036-48-9,138774-93-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In water; acetonitrile; for 3h; Ambient temperature;

DOI:10.1135/cccc19952170

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: 91.0%

3-pyridine propionic acid (3724-19-4) + Fmoc-Pro-OH (71989-31-6) + N-Fmoc L-Phe (35661-40-6) + Fmoc-Asn-OH (71989-16-7) + Fmoc-L-Arg-OH (91000-69-0,130752-32-8) + Nα-Fmoc-3-(1'-naphthyl)alanine (96402-49-2,138774-93-3) + trifluoroacetic acid (76-05-1) → C51H67N15O8*C2HF3O2

Guidance literature:

Fmoc-Asn-OH; With benzotriazol-1-ol; diisopropyl-carbodiimide; In N,N-dimethyl-formamide; for 2h;

With piperidine; In N,N-dimethyl-formamide; for 0.333333h;

3-pyridine propionic acid; Fmoc-Pro-OH; N-Fmoc L-Phe; Fmoc-L-Arg-OH; N^α-Fmoc-3-(1'-naphthyl)alanine; trifluoroacetic acid; Further stages;

DOI:10.1021/jm500599s

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

L-1-naphthylalanine

2-amino-3-(1-naphthyl)propanoic acid

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

Downstream raw materials:

C₅₅H₇₀N₁₀O₁₀

C₆₇H₇₈N₁₀O₁₀

Orn-D-Trp-Nal-Ile-D-Phe-His(1-Bzl)-NH₂

C₃₆H₄₄N₁₀O₅

Refernces

• 1、 Prochazka, Zdenko,Slaninova, Jirina. "THE 1- AND 2-NAPHTHYLALANINE ANALOGS OF OXYTOCIN AND VASOPRESSIN". . p. 2170 - 2177. Retrieved 2007/10/03.