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Boc-D-Phe(4-Me)-OH

  • CAS No. 80102-27-8

  • Cat. No. CS-0153094
  • Purity≥98%
  • MDL No.MFCD01317726

*For research and further manufacturing use only, not for direct human use.

Boc-D-Phe(4-Me)-OH|CS-0153094

Structure of 80102-27-8

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General Information

  • CAS No. 80102-27-8
  • Cat. No. CS-0153094
  • Purity ≥98%
  • MDL No. MFCD01317726
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₂₁NO₄
  • Molecular Weight 279.33
  • Synonym(s) Boc-D-4-Methylphenylalanine
  • SMILES CC1=CC=C(C[C@@H](NC(OC(C)(C)C)=O)C(O)=O)C=C1

Description

Boc-D-Phe(4-Me)-OH features a para-methyl-substituted phenylalanine scaffold with a tert-butoxycarbonyl (Boc) protecting group, enabling straightforward incorporation into peptide sequences. The methylated aromatic ring enhances lipophilicity and metabolic stability, while the Boc moiety ensures compatibility with standard Fmoc-based solid-phase synthesis protocols. This derivative serves as a key building block for bioactive peptide analogs requiring D-amino acid substitution and side-chain hydrophobicity.

Application

Boc-D-Phe(4-Me)-OH serves as a valuable chiral building block for the synthesis of D-peptide analogs and bioactive oligomers. The 4-methyl substituent enhances metabolic stability and conformational rigidity, while the Boc group provides reliable protection for amine-directed coupling reactions. This derivative exhibits excellent bench stability, compatibility with standard peptide coupling protocols, and facilitates efficient purification via common chromatographic methods.

Synthesis

  • Route1
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      178413-84-8
    • ~%
    • In-stock
      Boc-D-Phe(4-Me)-OH|CS-0153094
      80102-27-8

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 20, # 19 p. 5607 - 5612

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P280-P302+P352

Quality Control

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Computational Chemistry Data

  • TPSA   75.63
  • LogP   2.51542
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   4

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