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Tert-butyl (S)-(1-(benzyloxy)-3-hydroxypropan-2-yl)carbamate

  • CAS No. 79069-15-1

  • Cat. No. CS-0169628
  • Purity≥98%
  • MDL No.MFCD00235945

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

Tert-butyl (S)-(1-(benzyloxy)-3-hydroxypropan-2-yl)carbamate|CS-0169628

Structure of 79069-15-1

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General Information

  • CAS No. 79069-15-1
  • Cat. No. CS-0169628
  • Purity ≥98%
  • MDL No. MFCD00235945
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₂₃NO₄
  • Molecular Weight 281.35
  • Synonym(s) tert-Butyl [(1S)-2-hydroxy-1-[[(phenylmethyl)oxy]methyl]ethyl]carbamate
  • SMILES O=C(OC(C)(C)C)N[C@@H](CO)COCC1=CC=CC=C1

Description

This chiral building block features a protected hydroxyl group and a stereogenic center, enabling selective functionalization in asymmetric synthesis. The tert-butyl carbamate moiety provides stability under basic conditions, while the benzyloxy substituent offers orthogonal protection for downstream deprotection strategies.

Application

tert-Butyl (S)-(1-(benzyloxy)-3-hydroxypropan-2-yl)carbamate serves as a chiral building block for the synthesis of β-amino alcohols and related scaffolds. The molecule combines a labile benzyloxy group, a stable tert-butyl carbamate (Boc) protecting group, and a stereogenic center, enabling selective transformations in peptide and heterocyclic synthesis. Its bench-stable nature and orthogonal protection profile facilitate efficient multi-step sequences with minimal epimerization.

Synthesis

  • Route1

    References

    • Donner Tetrahedron Letters, 1995 , vol. 36, # 8 p. 1223 - 1226
  • Route2
    • null|null
      66866-45-3
    • ~%
    • In-stock
      Tert-butyl (S)-(1-(benzyloxy)-3-hydroxypropan-2-yl)carbamate|CS-0169628
      79069-15-1

    References

    • Synthetic Communications, , vol. 26, # 13 p. 2511 - 2522
  • Route3
    • (S)-2,5-Dioxopyrrolidin-1-yl 3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoate|CS-0154515
      13650-73-2
    • ~%
    • In-stock
      Tert-butyl (S)-(1-(benzyloxy)-3-hydroxypropan-2-yl)carbamate|CS-0169628
      79069-15-1

    References

    • EP1481976 A1, ; Page 226 ;

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-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   67.79
  • LogP   2.0888
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   6

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