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CS-W001157 4
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N-tert-Butoxycarbonyl-D-tyrosine methyl ester

  • CAS No. 76757-90-9

  • Cat. No. CS-M3313
  • Purity≥98%
  • MDL No.MFCD00057824

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

N-tert-Butoxycarbonyl-D-tyrosine methyl ester|CS-M3313

Structure of 76757-90-9

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General Information

  • CAS No. 76757-90-9
  • Cat. No. CS-M3313
  • Purity ≥98%
  • MDL No. MFCD00057824
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₂₁NO₅
  • Molecular Weight 295.33
  • Synonym(s) None
  • SMILES OC1=CC=C(C[C@@H](NC(OC(C)(C)C)=O)C(OC)=O)C=C1

Description

N-tert-Butoxycarbonyl-D-tyrosine methyl ester features a protected D-tyrosine scaffold with orthogonal functional handles: a tert-butoxycarbonyl group for amine shielding and a methyl ester for carboxylate protection. This dual protection enables stable incorporation into peptide sequences under standard coupling conditions, facilitating efficient synthesis of D-amino acid-containing peptides without racemization.

Application

N-tert-Butoxycarbonyl-D-tyrosine methyl ester serves as a stable, bench-ready building block for the synthesis of D-tyrosine-containing peptides and peptidomimetics. The tert-butoxycarbonyl (Boc) group provides reliable protection of the amine under acidic conditions, while the methyl ester facilitates straightforward hydrolysis or further derivatization. Its orthogonal functionality enables efficient incorporation into complex scaffolds via standard coupling protocols.

Synthesis

  • Route1

    References

    • ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; HAN, Sangdon; BUZARD, Daniel J.; LEHMANN, Juerg; NARAYANAN, Sanju; YUE, Dawei Patent: WO2011/127051 A1, 2011 ; Location in patent: Page/Page column 191 ; WO 2011/127051 A1
  • Route2

    References

    • Hulme, Alison N.; Rosser, Edward M. Organic Letters, 2002 , vol. 4, # 2 p. 265 - 267
  • Route3

    References

    • Tetrahedron, , vol. 61, # 45 p. 10748 - 10756

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-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   84.86
  • LogP   2.001
  • H_Acceptors   5
  • H_Donors   2
  • Rotatable_Bonds   4

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