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CS-W001157 4
Total: USD 88.00

Boc-Glu(OMe)-OMe

  • CAS No. 59279-60-6

  • Cat. No. CS-W008715
  • Purity≥97%
  • MDL No.MFCD03094774

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

Boc-Glu(OMe)-OMe|CS-W008715

Structure of 59279-60-6

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General Information

  • CAS No. 59279-60-6
  • Cat. No. CS-W008715
  • Purity ≥97%
  • MDL No. MFCD03094774
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₂₁NO₆
  • Molecular Weight 275.30
  • Synonym(s) N-tert-Butoxycarbonyl-L-glutamic acid dimethyl ester
  • SMILES COC(CC[C@@H](C(OC)=O)NC(OC(C)(C)C)=O)=O

Description

Boc-Glu(OMe)-OMe serves as a protected glutamic acid derivative featuring methyl ester groups at both carboxyl termini and a tert-butoxycarbonyl group on the α-amino function. This configuration enables direct incorporation into peptide synthesis workflows without side-chain protection adjustments, offering enhanced stability and simplified purification under standard conditions.

Application

Boc-Glu(OMe)-OMe serves as a versatile diester building block for the synthesis of glutamic acid-derived peptides and heterocyclic scaffolds. Its orthogonal protection—tert-butoxycarbonyl (Boc) at the α-amino group and methyl esters at both carboxyl termini—enables selective deprotection and sequential coupling in solid-phase and solution-phase syntheses. The compound exhibits excellent bench stability, facilitates straightforward purification, and functions reliably in standard peptide coupling protocols, making it a practical choice for medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • Varala, Ravi; Nuvula, Sreelatha; Adapa, Srinivas R. Journal of Organic Chemistry, 2006 , vol. 71, # 21 p. 8283 - 8286
  • Route2

    References

    • Goswami, Koushik; Paul, Sibasish; Bugde, Sandesh T.; Sinha, Surajit Tetrahedron, 2012 , vol. 68, # 1 p. 280 - 286
  • Route3

    References

    • Arda, Ana; Soengas, Raquel G.; Nieto, M. Isabel; Jimenez, Carlos; Rodriguez, Jaime Organic Letters, 2008 , vol. 10, # 11 p. 2175 - 2178

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   90.93
  • LogP   1.0059
  • H_Acceptors   6
  • H_Donors   1
  • Rotatable_Bonds   5

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