Fmoc-N-Me-Ile-OH

Base Information

• Chemical Name: Fmoc-N-Me-Ile-OH
• CAS No.: 138775-22-1
• Molecular Formula: C22H25NO4
• Molecular Weight: 367.445
• Hs Code.: 2924 29 70
• DSSTox Substance ID: DTXSID70572729
• Nikkaji Number: J2.831.134F
• Wikidata: Q72478638
• Mol file: 138775-22-1.mol

Synonyms:Fmoc-N-Me-Ile-OH;138775-22-1;Fmoc-N-methyl-L-isoleucine;Fmoc-N-Me-lle-OH;N-Fmoc-N-methyl-L-isoleucine;(2S,3S)-2-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]-3-methylpentanoic acid;L-Isoleucine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methyl-;N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-alpha-methyl-L-isoleucine;(2S,3S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-methylpentanoic acid;N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-N-methyl-L-isoleucine;N-{[(9H-Fluoren-9-yl)methoxy]carbonyl}-N-methyl-L-isoleucine;MFCD00153389;(2S,3S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}(methyl)amino)-3-methylpentanoic acid;Fmoc-MeIle-OH;Fmoc-L-MeIle-OH;N-methyl-N-fmoc-l-isoleucine;SCHEMBL1740175;DTXSID70572729;AKOS015909927;AM81859;CS-W008555;HY-W008555;DS-15025;F1129;F12341;M03363;EN300-1662995;A807437;J-007174;Fmoc-N-Me-Ile-OH, >=98% (sum of enantiomers, HPLC);S-138775-22-1;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-N-methyl-L-isoleucine;(2S,3S)-2-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]-3-methyl-pentanoic acid

Chemical Property of Fmoc-N-Me-Ile-OH

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 2.25E-12mmHg at 25°C
• Melting Point: 177-183 °C
• Refractive Index: 1.581
• Boiling Point: 537.3 °C at 760 mmHg
• PKA: 3.94±0.22(Predicted)
• Flash Point: 278.7 °C
• PSA: 66.84000
• Density: 1.194 g/cm³
• LogP: 4.36660
• Storage Temp.: 2-8°C
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 367.17835828
• Heavy Atom Count: 27
• Complexity: 514

Purity/Quality:

98% ^*data from raw suppliers

Fmoc-N-Me-Ile-OH ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C(C(=O)O)N(C)C(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: CC[C@H](C)[C@@H](C(=O)O)N(C)C(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Uses: Fmoc-N-Me-Ile-OH is a useful intermediate used in the total synthesis of Nannocystin A, a 21-membered cyclodepsipeptide with anticancer properties.

Technology Process of Fmoc-N-Me-Ile-OH

There total 6 articles about Fmoc-N-Me-Ile-OH 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%

N-Fmoc-N-methyl-L-isoleucine benzhydryl ester (1220527-63-8) → N-Fmoc-N-methyl-L-isoleucine (138775-22-1,1356090-81-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; toluene; at 20 ℃; for 1h;

DOI:10.1007/s00726-008-0221-8

Reference yield: 89.0%

3-methyl-2-(4-nitrophenylsulphonamido)pentanoic acid (852852-81-4) + diazomethane (186581-53-3,908094-01-9,334-88-3) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → N-Fmoc-N-methyl-L-isoleucine (138775-22-1,1356090-81-7)

Guidance literature:

Multistep reaction.;

DOI:10.1021/jo070075m

Reference yield: 70.0%

N-methyl-N-nosyl-L-isoleucine phenacyl ester (1208119-61-2) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → N-Fmoc-N-methyl-L-isoleucine (138775-22-1,1356090-81-7)

Guidance literature:

N-methyl-N-nosyl-L-isoleucine phenacyl ester; With sodium thiophenolate; In N,N-dimethyl-formamide; at 20 ℃; for 3h; Inert atmosphere;

With sodium carbonate; In water; pH=9;

(fluorenylmethoxy)carbonyl chloride; In 1,4-dioxane; at 0 ℃;

DOI:10.1021/jo901643f

upstream raw materials:

N-methyl-L-isoleucine

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

3-methyl-2-(4-nitrophenylsulphonamido)pentanoic acid

diazomethane

Downstream raw materials:

Fmoc-NMeIle-Thr-OBn

Refernces

• 1、 Leggio, Antonella,Belsito, Emilia Lucia,De Marco, Rosaria,Liguori, Angelo,Perri, Francesca,Viscomi, Maria Caterina. "An efficient preparation of N-Methyl-α-amino acids from N-Nosyl-α-amino acid phenacyl esters". experimental part. p. 1386 - 1392. Retrieved 2010/06/11.
• 2、 Di Gioia, Maria Luisa,Leggio, Antonella,Liguori, Angelo,Perri, Francesca. "Solid-phase synthesis of N-nosyl- and N-Fmoc-N-methyl-α-amino acids". . p. 3723 - 3728. Retrieved 2008/02/05.