Fmoc-L-beta-homoleucine

Base Information

• Chemical Name: Fmoc-L-beta-homoleucine
• CAS No.: 193887-44-4
• Molecular Formula: C22H25NO4
• Molecular Weight: 367.445
• DSSTox Substance ID: DTXSID90375815
• Nikkaji Number: J868.552E
• Wikidata: Q72478509
• Mol file: 193887-44-4.mol

Synonyms:193887-44-4;Fmoc-L-beta-homoleucine;Fmoc-beta-Holeu-OH;Fmoc-|A-HoLeu-OH;(3S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-5-methylhexanoic acid;(S)-3-(Fmoc-amino)-5-methylhexanoic acid;Fmoc-L-|A-HoLeu-OH;(3S)-3-({[(9H-FLUOREN-9-YL)METHOXY]CARBONYL}AMINO)-5-METHYLHEXANOIC ACID;MFCD01863059;Fmoc-L-|A-Homo-Leu-OH;Fmoc-L-beta-HLeu-OH;Fmoc-beta-Homo-Leu-OH;Fmoc-Leu-(C#CH2)OH;SCHEMBL119197;DTXSID90375815;Fmoc--HoLeu-OH Fmoc--homoleucine;Fmoc-beta-Homoleu-OH, >=96.0%;(3S)-3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-5-methylhexanoic acid;(S)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-methylhexanoic acid;AKOS015900953;CS-W011805;HY-W011089;AC-22079;AS-57913;F1268;EN300-755412;F12326;A813671;[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-fA-homoleucine;4-(2-OXO-2,3-DIHYDRO-1H-INDOL-3-YL)BUTANOICACID;S-193887-44-4;(S)-3-(9H-Fluorene-9-ylmethoxycarbonylamino)-5-methylhexanoic acid;Hexanoic acid,3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-5-methyl-,(3S)-

Chemical Property of Fmoc-L-beta-homoleucine

Chemical Property:

• Vapor Pressure: 6.3E-14mmHg at 25°C
• Melting Point: 110 °C
• Refractive Index: 1.576
• Boiling Point: 572.1 °C at 760 mmHg
• PKA: 4.40±0.10(Predicted)
• Flash Point: 299.8 °C
• PSA: 75.63000
• Density: 1.189 g/cm³
• LogP: 4.80540
• Storage Temp.: 2-8°C
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 367.17835828
• Heavy Atom Count: 27
• Complexity: 498

Purity/Quality:

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

Fmoc-l-β-homoleucine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(CC(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: CC(C)C[C@@H](CC(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Uses: Fmoc-l-beta-homoleucine

Technology Process of Fmoc-L-beta-homoleucine

There total 6 articles about Fmoc-L-beta-homoleucine 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: 94.0%

(S)-(9H-fluoren-9-yl)methyl (1-diazo-5-methyl-2-oxohexan-3-yl)carbamate (193954-24-4) → (S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-5-methylhexanoic acid (193887-44-4,1335042-37-9,212688-54-5)

Guidance literature:

With silver trifluoroacetate; silica gel; In ethyl acetate; at 50 ℃; for 0.25h;

DOI:10.1080/00397910500290466

Reference yield: 53.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + Fmoc-Leu-OH (35661-60-0) → (S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-5-methylhexanoic acid (193887-44-4,1335042-37-9,212688-54-5)

Guidance literature:

Fmoc-Leu-OH; With TEA; isobutyl chloroformate; In tetrahydrofuran; diethyl ether; at 0 ℃;

diazomethane; In diethyl ether;

With silver trifluoroacetate; sodium carbonate; sodium thiosulfate; In 1,4-dioxane; Further stages.;

DOI:10.1039/b106368p

Reference yield:

Fmoc-Leu-OH (35661-60-0) → (S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-5-methylhexanoic acid (193887-44-4,1335042-37-9,212688-54-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) i-BuOCOCl, NMM / 1.) THF, -20 deg C, 20 min, 2.) THF, Et₂O, -5 deg C, 4 h

2: 66 percent / CF₃COOAg, Et₃N / tetrahydrofuran; H₂O

With 4-methyl-morpholine; silver trifluoroacetate; triethylamine; isobutyl chloroformate; In tetrahydrofuran; water;

DOI:10.1002/hlca.19980810202

upstream raw materials:

(S)-(9H-fluoren-9-yl)methyl (1-diazo-5-methyl-2-oxohexan-3-yl)carbamate

diazomethane

Fmoc-Leu-OH

C₂₄H₂₇NO₆

Downstream raw materials:

(S)-3-amino-5-methylhexanoic acid

9-methylene-fluorene

Refernces

• 1、 Coffey,Drauz,Roberts,Skidmore,Smith. "beta-peptides as catalysts: poly-beta-leucine as a catalyst for the Julia-Colonna asymmetric epoxidation of enones.". . p. 2330 - 2331. Retrieved 2007/10/03.
• 2、 Guichard, Gilles,Abele, Stefan,Seebach, Dieter. "Preparation of N-Fmoc-Protected β2- and β3-Amino Acids and Their Use as Building Blocks for the Solid-Phase Synthesis of β-Peptides". . p. 187 - 206. Retrieved 2007/10/03.