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CS-W001157 4
Total: USD 88.00

1,1-Dimethylethyl (4R)-4-hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylate

  • CAS No. 108149-63-9

  • Cat. No. CS-0011755
  • Purity≥97%
  • MDL No.MFCD06202686

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

1,1-Dimethylethyl (4R)-4-hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylate|CS-0011755

Structure of 108149-63-9

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General Information

  • CAS No. 108149-63-9
  • Cat. No. CS-0011755
  • Purity ≥97%
  • MDL No. MFCD06202686
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₂₁NO₄
  • Molecular Weight 231.29
  • Synonym(s) 3-Oxazolidinecarboxylic acid, 4-(hydroxymethyl)-2,2-dimethyl-, 1,1-dimethylethyl ester, (R)-; (R)-4-Hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester; tert-butyl (4R)-4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
  • SMILES OC[C@@H]1COC(C)(C)N1C(OC(C)(C)C)=O

Description

This oxazolidine derivative features a chiral hydroxymethyl group and a tert-butyl ester, enabling stereocontrolled synthesis in medicinal chemistry. The bench-stable, moisture-tolerant scaffold integrates readily into complex molecular architectures, offering high functional group compatibility for peptide and heterocyclic compound development.

Application

1,1-Dimethylethyl (4R)-4-hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylate serves as a robust chiral synthon for the construction of oxazolidine-based scaffolds. The protected hydroxymethyl group enables selective derivatization, while the oxazolidine core provides excellent functional group tolerance and bench stability. This compound facilitates stereoselective transformations in peptide-like sequence synthesis and offers straightforward deprotection under mild acidic conditions, making it well-suited for iterative synthetic workflows.

Synthesis

  • Route1

    References

    • CHUGAI SEIYAKU KABUSHIKI KAISHA Patent: WO2005/87700 A2, 2005 ; Location in patent: Page/Page column 322 ; WO 2005/087700 A2
  • Route2

    References

    • Garner, Philip; Park, Jung Min Journal of Organic Chemistry, 1987 , vol. 52, # 12 p. 2361 - 2364
  • Route3

    References

    • Journal of Organic Chemistry, , vol. 72, # 4 p. 1218 - 1225

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   59
  • LogP   1.3507
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   1

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