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Carbamic acid, (tetrahydro-5-oxo-3-furanyl)-, 1,1-dimethylethyl ester, (S)-

  • CAS No. 104227-71-6

  • Cat. No. CS-0030561
  • Purity≥97%
  • MDL No.None

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

Carbamic acid, (tetrahydro-5-oxo-3-furanyl)-, 1,1-dimethylethyl ester, (S)-|CS-0030561

Structure of 104227-71-6

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General Information

  • CAS No. 104227-71-6
  • Cat. No. CS-0030561
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₅NO₄
  • Molecular Weight 201.22
  • Synonym(s) tert-butyl [(3S)-5-oxotetrahydrofuran-3-yl]carbamate
  • SMILES O=C(OC(C)(C)C)N[C@@H](C1)COC1=O

Description

This chiral carbamate features a bench-stable, moisture-tolerant tert-butyl group attached to a stereodefined tetrahydrofuran ring. The 5-oxo functionality enables selective transformations at the C5 position, while the carbamate handles nitrogen protection efficiently in asymmetric synthesis workflows.

Application

(S)-tert-Butyl (5-oxotetrahydrofuran-3-yl)carbamate serves as a valuable chiral building block in synthetic organic chemistry, enabling stereoselective access to oxygen-containing heterocycles. The molecule features a stable, bench-ready carbamate-protected amine and a ketone functionality at C5, both of which participate reliably in standard transformations such as reductive amination, nucleophilic addition, and enolate chemistry. Its defined stereochemistry and compatibility with common reaction conditions make it well-suited for the construction of complex intermediates in medicinal chemistry and natural product synthesis.

Synthesis

  • Route1

    References

    • Canadian Journal of Chemistry, , vol. 71, # 9 p. 1407 - 1411
  • Route2

    References

    • Organic Letters, , vol. 6, # 1 p. 19 - 22
  • Route3
    • null|null
      651036-65-6
    • ~49%
    • In-stock
      Carbamic acid, (tetrahydro-5-oxo-3-furanyl)-, 1,1-dimethylethyl ester, (S)-|CS-0030561
      104227-71-6

    References

    • Tetrahedron, , vol. 61, # 13 p. 3403 - 3417

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   64.63
  • LogP   0.8266
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   1

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