(R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-methylpentanoic acid

Base Information

• Chemical Name: (R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-methylpentanoic acid
• CAS No.: 172695-33-9
• Molecular Formula: C21H23NO4
• Molecular Weight: 353.418
• DSSTox Substance ID: DTXSID90375830
• Nikkaji Number: J868.551G
• Wikidata: Q72478483
• Mol file: 172695-33-9.mol

Synonyms:172695-33-9;Fmoc-L-beta-homovaline;(R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-methylpentanoic acid;Fmoc-|A-HoVal-OH;Fmoc-beta-HoVal-OH;(3R)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methylpentanoic acid;MFCD01862853;(3R)-3-({[(9H-Fluoren-9-yl)methoxy]carbonyl}amino)-4-methylpentanoic acid;(R)-3-(Fmoc-amino)-4-methylpentanoic acid;Fmoc-L-beta-HVal-OH;Fmoc-beta-Homo-Val-OH;Fmoc-Val-(C#CH2)OH;SCHEMBL119762;DTXSID90375830;KFDMTAMWOIQTOB-LJQANCHMSA-N;Fmoc--HoVal-OH Fmoc-L--homovaline;AKOS015911964;CS-W013901;HY-W013185;AS-47152;Fmoc-beta-Leu-OH, >=97.0% (HPLC);EN300-816471;F12331;A811443;N-beta-(9-Fluorenylmethyloxycarbonyl)-L-homovaline;S-172695-33-9;(R)-3-(9H-Fluorene-9-ylmethoxycarbonylamino)-4-methylvaleric acid;(3R)-3-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino]-4-methylpentanoic acid;3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methyl-pentanoic acid;(R)-3-(Fmoc-amino)-4-methylpentanoic Acid

Chemical Property of (R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-methylpentanoic acid

Chemical Property:

• Vapor Pressure: 1.49E-13mmHg at 25°C
• Melting Point: 153-154 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• Refractive Index: 1.582
• Boiling Point: 563.926 °C at 760 mmHg
• PKA: 4.41±0.10(Predicted)
• Flash Point: 294.852 °C
• PSA: 75.63000
• Density: 1.208 g/cm³
• LogP: 4.41530
• Storage Temp.: 2-8°C
• Water Solubility.: Slightly soluble in water.
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 353.16270821
• Heavy Atom Count: 26
• Complexity: 484

Purity/Quality:

99% ^*data from raw suppliers

Fmoc-L-β-homovaline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(CC(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: CC(C)[C@@H](CC(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Uses: N-Fmoc-L-beta-homovaline is used as pharmaceutical intermediate.

Technology Process of (R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-methylpentanoic acid

There total 16 articles about (R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-methylpentanoic acid 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%

(S)-(9H-fluoren-9-yl)methyl (1-diazo-4-methyl-2-oxopentan-3-yl)carbamate (193148-58-2) → Fmoc-β3-HVal (172695-33-9)

Guidance literature:

With water; silver benzoate; In 1,4-dioxane; at 70 ℃; for 5h;

Reference yield: 91.0%

(R)-2-(N-fluorenylmethoxycarbonylamino)-3-methylbutyl cyanide (172695-31-7) → Fmoc-β3-HVal (172695-33-9)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; for 8h; Heating;

DOI:10.1016/0040-4020(95)00778-7

Reference yield:

Fmoc-Val-OH (68858-20-8) → Fmoc-β3-HVal (172695-33-9)

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: 75 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:

(R)-2-(N-fluorenylmethoxycarbonylamino)-3-methylbutyl cyanide

(S)-(9H-fluoren-9-yl)methyl (1-diazo-4-methyl-2-oxopentan-3-yl)carbamate

Fmoc-Val-OH

C₂₃H₂₅NO₆

Downstream raw materials:

C₆₇H₁₂₂N₂₀O₁₁

β³Tyr-(ACHC-β³Val-β³Arg)3

C₃₈H₄₃N₅O₈

Refernces

• 1、 Vishwanatha, Thimmalapura M.,Giepmans, Ben,Goda, Sayed K.,D?mling, Alexander. "Tubulysin Synthesis Featuring Stereoselective Catalysis and Highly Convergent Multicomponent Assembly". supporting information. p. 5396 - 5400. Retrieved 2020/07/08.
• 2、 Kantharaju,Suresh Babu, Vommina V.. "Homologation of α-amino acids to β-amino acids: 9-Fluorenylmethyl chloroformate as a carboxyl group activating agent for the synthesis of Nα-protected aminoacyldiazomethanes". . p. 2152 - 2158. Retrieved 2007/10/03.