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CS-W001157 4
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(R)-2-((tert-Butoxycarbonyl)amino)-3-methoxypropanoic acid

  • CAS No. 86123-95-7

  • Cat. No. CS-D0906
  • Purity≥97%
  • MDL No.MFCD08063987

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

(R)-2-((tert-Butoxycarbonyl)amino)-3-methoxypropanoic acid|CS-D0906

Structure of 86123-95-7

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General Information

  • CAS No. 86123-95-7
  • Cat. No. CS-D0906
  • Purity ≥97%
  • MDL No. MFCD08063987
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₇NO₅
  • Molecular Weight 219.24
  • Synonym(s) O-methyl-N-(phenylmethyl)-D-Serine methyl ester
  • SMILES O=C(O)[C@@H](COC)NC(OC(C)(C)C)=O

Description

(R)-2-((tert-Butoxycarbonyl)amino)-3-methoxypropanoic acid features a chiral center with defined (R)-stereochemistry, enabling precise incorporation into peptide backbones. The tert-butoxycarbonyl group provides stable N-terminal protection, while the methoxy substituent enhances solubility and modulates electronic properties. This derivative supports efficient synthesis of bioactive peptides under standard bench conditions.

Application

(R)-2-((tert-Butoxycarbonyl)amino)-3-methoxypropanoic acid serves as a valuable chiral building block for the synthesis of peptidomimetics and bioactive heterocycles. The protected amine and methoxy-functionalized side chain enable orthogonal reactivity in solid-phase and solution-phase synthesis. Bench-stable and readily purified by chromatography, it facilitates efficient access to complex scaffolds through standard coupling and cyclization protocols.

Synthesis

  • Route1
    • In-stock
      (S)-2-((tert-Butoxycarbonyl)amino)-3-hydroxypropanoic acid|CS-W015379
      3262-72-4
    • null|null
      77-78-1
    • ~99%
    • In-stock
      (R)-2-((tert-Butoxycarbonyl)amino)-3-methoxypropanoic acid|CS-D0906
      86123-95-7

    References

    • SCHWARZ PHARMA AG Patent: WO2006/37574 A1, 2006 ; Location in patent: Page/Page column 17-18 ;
  • Route2
    • Methyl N-(tert-butoxycarbonyl)-O-methyl-D-serinate|CS-0456538
      862372-14-3
    • ~99%
    • In-stock
      (R)-2-((tert-Butoxycarbonyl)amino)-3-methoxypropanoic acid|CS-D0906
      86123-95-7

    References

    • ASTRAZENECA AB; ASTRAZENECA UK LIMITED Patent: WO2005/75439 A1, 2005 ; Location in patent: Page/Page column 127 ; WO 2005/075439 A1
  • Route3
    • In-stock
      (S)-2-((tert-Butoxycarbonyl)amino)-3-hydroxypropanoic acid|CS-W015379
      3262-72-4
    • null|null
      74-88-4
    • ~%
    • In-stock
      (R)-2-((tert-Butoxycarbonyl)amino)-3-methoxypropanoic acid|CS-D0906
      86123-95-7

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 14, # 23 p. 5817 - 5822

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

Quality Control

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Computational Chemistry Data

  • TPSA   84.86
  • LogP   0.6107
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   4

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