Cas no 103478-63-3 (N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-N-methyl-D-leucine)

N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-N-methyl-D-leucine is a protected amino acid derivative widely used in peptide synthesis, particularly in solid-phase methodologies. Its key advantages include the presence of the fluorenylmethoxycarbonyl (Fmoc) protecting group, which ensures selective deprotection under mild basic conditions, enhancing compatibility with sensitive residues. The N-methyl modification improves metabolic stability and conformational flexibility in synthesized peptides. The D-leucine configuration offers resistance to enzymatic degradation, making it valuable in designing bioactive peptides with enhanced stability. This compound is highly soluble in common organic solvents, facilitating efficient coupling reactions. Its robust performance in orthogonal protection strategies makes it a preferred choice for researchers in medicinal chemistry and peptide engineering.
N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-N-methyl-D-leucine structure
103478-63-3 structure
Product Name:N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-N-methyl-D-leucine
CAS No:103478-63-3
MF:C22H25NO4
MW:367.43820643425
MDL:MFCD00235877
CID:62386
PubChem ID:329747435
Update Time:2025-05-22

N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-N-methyl-D-leucine Chemical and Physical Properties

Names and Identifiers

    • Fmoc-N-methyl-D-leucine
    • N-(9-Fluorenylmethyloxycarbonyl)-N-methyl-D-leucine
    • Fmoc-N-Me-D-Leu-OH
    • Fmoc-D-MeLeu-OH
    • Fmoc-Nalpha-methyl-D-leucine
    • Fmoc-N-Me-D-Leucine
    • Fmoc-N-Me-L-D-Leu-OH
    • (2R)-2-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]-4-methylpentanoic acid
    • fmoc-d-n-me-leu-oh
    • H-N-ME-D-ALA.HCL
    • REF DUPL: Fmoc-D-N-Me-Leu-OH
    • FMOC-N-ALPHA-METHYL-D-LEUCINE
    • N-ALPHA-FMOC-N-ALPHA-METHYL-D-LEUCINE
    • FMOC-N-METHYL-D-LEUCINE 98+%
    • N-FMoc-N-Methyl-D-leucine, 97%
    • Fmoc-N-methyl-D-leucine≥ 99% (HPLC)
    • D-Leucine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methyl-
    • (2R)-2-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]-4-methyl-pentanoic acid
    • PubChem18971
    • TMA027
    • FCH2721615
    • Fmoc-N-Me-D-Leu
    • N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-N-methyl-D-leucine
    • AKOS015908538
    • N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-alpha-methyl-D-leucine
    • HY-W011088
    • A800748
    • Fmoc-N-Me-D-Leu-OH, >=97.0%
    • (r)-2-((((9h-fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-4-methylpentanoic acid
    • SCHEMBL3728170
    • AKOS015837196
    • 103478-63-3
    • (2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}(methyl)amino)-4-methylpentanoic acid
    • DTXSID40427131
    • MFCD00235877
    • AMY22568
    • PD196793
    • F12340
    • J-000982
    • CS-W011804
    • AS-56975
    • AC-31991
    • (2R)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl](methyl)amino}-4-methylpentanoic acid
    • DB-038040
    • MDL: MFCD00235877
    • Inchi: 1S/C22H25NO4/c1-14(2)12-20(21(24)25)23(3)22(26)27-13-19-17-10-6-4-8-15(17)16-9-5-7-11-18(16)19/h4-11,14,19-20H,12-13H2,1-3H3,(H,24,25)/t20-/m1/s1
    • InChI Key: BUJQSIPFDWLNDC-HXUWFJFHSA-N
    • SMILES: O(C(N(C)[C@@H](C(=O)O)CC(C)C)=O)CC1C2C=CC=CC=2C2C=CC=CC1=2

Computed Properties

  • Exact Mass: 367.17800
  • Monoisotopic Mass: 367.17835828g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 27
  • Rotatable Bond Count: 7
  • Complexity: 512
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: 4.6
  • Topological Polar Surface Area: 66.8

Experimental Properties

  • Color/Form: No data available
  • Density: 1.1940
  • Melting Point: No data available
  • Boiling Point: 537.3±29.0 °C at 760 mmHg
  • Flash Point: 278.7±24.3 °C
  • Refractive Index: 1.581
  • Solubility: Soluble in clear solution (0.3 gram in 2 ml DMF).
  • PSA: 66.84000
  • LogP: 4.36660

N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-N-methyl-D-leucine Customs Data

  • HS CODE:2924299090
  • Customs Data:

    China Customs Code:

    2924299090

    Overview:

    2924299090. Other cyclic amides(Including cyclic carbamates)(Including their derivatives as well as their salts). VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:30.0%

    Declaration elements:

    Product Name, component content, use to, packing

    Summary:

    2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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Additional information on N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-N-methyl-D-leucine

N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-N-methyl-D-leucine: A Comprehensive Overview

N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-N-methyl-D-leucine, also known by its CAS number 103478-63-3, is a specialized amino acid derivative that has garnered significant attention in the fields of biochemistry and pharmacology. This compound is a modified version of D-leucine, a naturally occurring amino acid, with a unique substituent that enhances its functionality in various applications. The inclusion of the fluorenylmethoxycarbonyl (Fmoc) group and the methyl substitution provides this molecule with distinctive chemical properties, making it invaluable in modern research and industrial settings.

The structural composition of this compound is characterized by the presence of the Fmoc group, which is a well-known protecting group in peptide synthesis. The Fmoc moiety is attached to the nitrogen atom of the leucine residue, while a methyl group further modifies this nitrogen. This dual modification not only stabilizes the molecule but also imparts specific reactivity, enabling its use in complex chemical reactions. The D configuration of the leucine residue adds another layer of complexity, as it introduces chirality into the molecule, which is crucial for its biological activity.

Recent advancements in synthetic chemistry have led to improved methods for the synthesis and purification of N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-N-methyl-D-leucine. Researchers have explored various strategies to optimize the reaction conditions, ensuring high yields and purity levels. These improvements are particularly important for applications where precise control over molecular structure is essential, such as in drug discovery and biotechnology.

In terms of applications, this compound has found extensive use in peptide synthesis as a building block. The Fmoc group serves as an excellent protecting group due to its stability under basic conditions and ease of removal under acidic conditions. This property makes it ideal for solid-phase peptide synthesis (SPPS), where sequential addition of amino acids is required. Additionally, the methyl substitution on the nitrogen enhances solubility and stability, making it suitable for use in diverse solvent systems.

Recent studies have also highlighted the potential of N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-N-methyl-D-leucine in drug delivery systems. Its unique structure allows for the creation of bioactive molecules with tailored pharmacokinetic profiles. For instance, researchers have investigated its role in developing prodrugs that can be activated upon reaching specific tissues or cellular compartments. This approach not only enhances drug efficacy but also minimizes side effects by reducing systemic exposure.

The chirality introduced by the D configuration of leucine has been leveraged in enantioselective synthesis, where the formation of enantiomerically pure compounds is critical. This compound's ability to induce asymmetry in chemical reactions has made it a valuable tool in asymmetric catalysis, particularly in the synthesis of complex natural products and pharmaceutical intermediates.

In conclusion, N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-N-methyl-D-leucine stands out as a versatile and indispensable molecule in contemporary chemical research. Its unique structural features and functional groups make it a cornerstone in peptide synthesis, drug discovery, and asymmetric catalysis. As ongoing research continues to uncover new applications and optimize its synthesis, this compound will undoubtedly remain at the forefront of scientific innovation.

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