Fmoc-L-beta-homoisoleucine

Base Information

• Chemical Name: Fmoc-L-beta-homoisoleucine
• CAS No.: 193954-27-7
• Molecular Formula: C22H25NO4
• Molecular Weight: 367.445
• Mol file: 193954-27-7.mol

Synonyms:Fmoc-L-beta-homoisoleucine;193954-27-7;Fmoc-|A-HoIle-OH;1217622-60-0;Fmoc-beta-Hoile-OH;(3R,4S)-3-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-methylhexanoic acid;(3R,4S)-3-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino]-4-methylhexanoic acid;Fmoc-beta-Homoile-OH;(3R,4S)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-methylhexanoic acid;(3R,4S)-3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-methylhexanoic acid;(3R,4S)-Rel-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-methylhexanoic acid;(3R,4S)-3-(Fmoc-amino)-4-methylhexanoic acid;Fmoc-|A-Homo-Ile-OH;MFCD01862850;Fmoc-Ile-(C#CH2)OH;SCHEMBL119195;VHZUUIWBAYOCDD-VBKZILBWSA-N;AKOS016003206;CS-W009773;HY-W009057;Fmoc--HoIle-OH Fmoc-L--homoisoleucine;AM803448;AS-39460;Fmoc-beta-Homoile-OH, >=96.0% (HPLC);EN300-269068;(3R,4S)-Rel-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-methylhexanoicacid

Chemical Property of Fmoc-L-beta-homoisoleucine

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 6.3E-14mmHg at 25°C
• Melting Point: 98-100 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• Refractive Index: 1.576
• Boiling Point: 572.1 °C at 760 mmHg
• PKA: 4.41±0.10(Predicted)
• Flash Point: 299.8 °C
• PSA: 75.63000
• Density: 1.188 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: 500

Purity/Quality:

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

Fmoc-L-beta-homoisoleucine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Fmoc-L-beta-homoisoleucine

There total 4 articles about Fmoc-L-beta-homoisoleucine 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: 98.0%

Fmoc-L-isoleucyl(diazo)methane (193954-25-5) → Fmoc-β3-HIle-OH (193954-27-7)

Guidance literature:

With silver(I) acetate; triethylamine; In tetrahydrofuran; water;

DOI:10.1002/hlca.19980810107

Reference yield:

Fmoc-Ile-OH (71989-23-6,251316-98-0) → Fmoc-β3-HIle-OH (193954-27-7)

Guidance literature:

Multi-step reaction with 3 steps

1: NEt₃ / tetrahydrofuran / 0.25 h / -15 °C

2: tetrahydrofuran; diethyl ether / 3 h / Ambient temperature

3: silver benzoate, H₂O / dioxane / Ambient temperature

With water; silver benzoate; triethylamine; In tetrahydrofuran; 1,4-dioxane; diethyl ether;

DOI:10.1055/s-1998-2075

Reference yield:

C24H27NO6 → Fmoc-β3-HIle-OH (193954-27-7)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran; diethyl ether / 3 h / Ambient temperature

2: silver benzoate, H₂O / dioxane / Ambient temperature

With water; silver benzoate; In tetrahydrofuran; 1,4-dioxane; diethyl ether;

DOI:10.1055/s-1998-2075

upstream raw materials:

Fmoc-L-isoleucyl(diazo)methane

Fmoc-Ile-OH

Downstream raw materials:

C₂₈H₃₉BrN₄O₇

H-β2hSec(PMB)-β3hAla-β3hLeu-β3hIle-OH*TFA

C₆₇H₁₂₂N₂₀O₁₁

C₆₇H₁₂₂N₁₄O₁₁

Refernces

• 1、 Ellmerer-Mueller, Ernst P.,Broessner, Dagmar,Maslouh, Najib,Tako, Andreas. "Synthesis of N-{[(9H-Fluoren-9-yl)methoxy]carbonyl}-Protected (Fmoc) β-Amino Acids (= Homo-α-Amino Acids) by Direct Homologation". . p. 59 - 65. Retrieved 2007/10/03.