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CS-W001157 4
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(S)-isopropyl 2-(((S)-(perfluorophenoxy)(phenoxy)phosphoryl)amino)propanoate

  • CAS No. 1334513-02-8

  • Cat. No. CS-B0630
  • Purity≥96%
  • MDL No.MFCD22665799

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

(S)-isopropyl 2-(((S)-(perfluorophenoxy)(phenoxy)phosphoryl)amino)propanoate|CS-B0630

Structure of 1334513-02-8

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General Information

  • CAS No. 1334513-02-8
  • Cat. No. CS-B0630
  • Purity ≥96%
  • MDL No. MFCD22665799
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₈H₁₇F₅NO₅P
  • Molecular Weight 453.30
  • Synonym(s) None
  • SMILES C[C@H](N[P@](OC1=CC=CC=C1)(OC2=C(F)C(F)=C(F)C(F)=C2F)=O)C(OC(C)C)=O

Description

(S)-isopropyl 2-(((S)-(perfluorophenoxy)(phenoxy)phosphoryl)amino)propanoate features a chiral phosphoramidate scaffold with dual aryl ether moieties, combining perfluorophenyl and phenyl groups for enhanced stability and lipophilicity. This configuration enables efficient incorporation into nucleoside prodrug systems, facilitating targeted delivery and controlled activation in metabolic pathways.

Application

(S)-Isopropyl 2-(((S)-(perfluorophenoxy)(phenoxy)phosphoryl)amino)propanoate serves as a chiral phosphoramidate building block for the synthesis of stereodefined oligonucleotides and phosphorylated bioactive molecules. Its perfluorophenoxy and phenoxy groups enable efficient coupling under standard conditions, while the (S)-configuration ensures high stereocontrol in phosphorus-centered transformations. The compound exhibits excellent bench stability, simplifies purification, and functions reliably in automated solid-phase synthesis workflows.

Synthesis

  • Route1

    References

    • WO2010/135569 A1, ; Page/Page column 52-53 ; WO 2010/135569 A1
  • Route2

    References

    • WO2012/142085 A1, ; Page/Page column 74-75 ;
  • Route3

    References

    • Journal of Organic Chemistry, , vol. 76, # 20 p. 8311 - 8319

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   73.86
  • LogP   4.8777
  • H_Acceptors   5
  • H_Donors   1
  • Rotatable_Bonds   8

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