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CS-W001157 4
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Methyl (R)-(+)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-oxazolidinecarboxylate

  • CAS No. 95715-86-9

  • Cat. No. CS-D1220
  • Purity≥95%
  • MDL No.MFCD00674041

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

Methyl (R)-(+)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-oxazolidinecarboxylate|CS-D1220

Structure of 95715-86-9

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General Information

  • CAS No. 95715-86-9
  • Cat. No. CS-D1220
  • Purity ≥95%
  • MDL No. MFCD00674041
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₂₁NO₅
  • Molecular Weight 259.30
  • Synonym(s) (R)-Methyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-oxazolidinecarboxylate; Methyl (R)-3-(T-butoxycarbonyl)-2,2-di-me-4-oxaz
  • SMILES O=C([C@H]1COC(C)(C)N1C(OC(C)(C)C)=O)OC

Description

Methyl (R)-(+)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-oxazolidinecarboxylate is a chiral oxazolidine derivative featuring a sterically hindered tert-butyl carbamate group and a methyl ester. This configuration enables reliable asymmetric synthesis applications in peptide and heterocyclic chemistry. The compound exhibits bench-stable handling characteristics and integrates efficiently into multi-step synthetic sequences.

Application

Methyl (R)-(+)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-oxazolidinecarboxylate serves as a stereochemically defined chiral building block for the synthesis of peptidomimetics and heterocyclic scaffolds. Its stable oxazolidine core enables efficient functionalization at C4, while the tert-butoxycarbonyl group provides orthogonal protection for amine intermediates. The molecule exhibits excellent bench stability and facilitates straightforward purification, making it well-suited for iterative synthetic sequences in medicinal chemistry and process development workflows.

Synthesis

  • Route1
    • In-stock
      Boc-Ser-OMe|CS-W009216
      2766-43-0
    • null|null
      77-76-9
    • ~94%
    • In-stock
      Methyl (R)-(+)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-oxazolidinecarboxylate|CS-D1220
      95715-86-9

    References

    • Uchida, Hideharu; Nishida, Atsushi; Nakagawa, Masako Tetrahedron Letters, 1999 , vol. 40, # 1 p. 113 - 116
  • Route2

    References

    • Journal of Medicinal Chemistry, , vol. 49, # 11 p. 3064 - 3067
  • Route3

    References

    • Organic Letters, , vol. 5, # 23 p. 4253 - 4256

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H227-H315-H319-H335
Precautionary Statements : P210-P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P370+P378-P403-P405-P501

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Computational Chemistry Data

  • TPSA   65.07
  • LogP   1.5314
  • H_Acceptors   5
  • H_Donors   0
  • Rotatable_Bonds   1

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