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(S)-2-((tert-Butoxycarbonyl)amino)-6-hydroxyhexanoic acid

  • CAS No. 77611-37-1

  • Cat. No. CS-0179118
  • Molecule weight247.29
  • Purity≥97%
  • MDL No.None

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

(S)-2-((tert-Butoxycarbonyl)amino)-6-hydroxyhexanoic acid|CS-0179118

Structure of 77611-37-1

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General Information

  • CAS No. 77611-37-1
  • Cat. No. CS-0179118
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₂₁NO₅
  • Molecular Weight 247.29
  • Synonym(s) Boc-L-6-hydroxynorleucine
  • SMILES CC(C)(OC(N[C@H](C(O)=O)CCCCO)=O)C

Description

This chiral building block features a protected amine and a hydroxyl group flanking a six-carbon chain, enabling direct incorporation into peptide architectures. The tert-butyl carbamate handle ensures orthogonal deprotection, while the pendant hydroxy function offers a site for selective derivatization or glycosylation.

Application

(S)-2-((tert-Butoxycarbonyl)amino)-6-hydroxyhexanoic acid serves as a versatile chiral building block for peptide and heterocyclic synthesis, enabling efficient access to bioactive scaffolds. The protected amine and terminal hydroxyl group provide orthogonal functionality for sequential derivatization, while the tert-butoxycarbonyl (Boc) group ensures bench stability and compatibility with standard coupling protocols. Its structure facilitates straightforward purification and integration into multi-step syntheses of complex molecules.

Synthesis

  • Route1

    References

    • Matsumoto, Naoki; Kaneko, Katsura; Nagai, Hazuki; Konuki, Kaname; Tsuchida, Toshio; Issiki, Kunio Patent: US2004/249205 A1, 2004 ; Location in patent: Page 3 ;
  • Route2

    References

    • Rumsh; Mikhailova; Mikhura; Prudchenko; Chikin; Mikhaleva; Kaliberda; Dergousova; Mel'Nikov; Formanovskii Russian Journal of Bioorganic Chemistry, 2008 , vol. 34, # 6 p. 660 - 667
  • Route3

    References

    • Keystone Biomedical, Inc. Patent: US6335443 B1, 2002 ; Location in patent: Page column 8 ;

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   95.86
  • LogP   1.1269
  • H_Acceptors   4
  • H_Donors   3
  • Rotatable_Bonds   6

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