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(R)-tert-Butyl1-(benzylamino)-3-methoxy-1-oxopropan-2-ylcarbamate

  • CAS No. 880468-89-3

  • Cat. No. CS-0006747
  • Purity≥98%
  • MDL No.MFCD16620517

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

(R)-tert-Butyl1-(benzylamino)-3-methoxy-1-oxopropan-2-ylcarbamate|CS-0006747

Structure of 880468-89-3

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General Information

  • CAS No. 880468-89-3
  • Cat. No. CS-0006747
  • Purity ≥98%
  • MDL No. MFCD16620517
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₆H₂₄N₂O₄
  • Molecular Weight 308.37
  • Synonym(s) O-methyl-N-alpha-[phenylmethoxy]carbonyl]-N-(phenylmethyl)-D-Serinamide
  • SMILES O=C(OC(C)(C)C)N[C@H](COC)C(NCC1=CC=CC=C1)=O

Description

This orthogonally-protected diaminopropionic acid derivative is based on the hindered Dde variant ivDde. The side-chain ivDde group is considerably more stable to piperidine than Dde and is less prone to migrate from protected to unprotected side-chains [1]. However, migration from side-chain to the unprotected -amino group of Dpr is unavoidable [2]. This side-reaction can, however, be minimized by the appropriate choice of coupling method for the subsequent residue, see [3].When removing ivDde in the presence of allyl-based protecting groups, allyl alcohol should be included in the deprotection solution to prevent reduction of the allyl group [4]. Associated Protocols and Technical ArticlesCleavage and Deprotection Protocols for Fmoc SPPSLiterature references[1] S. R. Chhabra, et al. (1998) Tetrahedron Lett., 39, 1603. [2] R. Wilhelm, et al., Poster 34 presented at the 16th American Peptide Symposium, Minneapolis, 1999. [3] J. Beythien & P. Schneeberger, in Peptides 2000, Proc. 26th European Peptide Symposium, EDK, Paris, 2001, pp. 361. [4] B. Rohwedder, et al. (1998) Tetrahedron Lett., 39, 1175.

Synthesis

  • Route1

    References

    • MSN LABORATORIES LIMITED; SATYANARAYANA REDDY, Manne; ESWARAIAH, Sajja; SRINIVAS, Aluru; SATYANARAYANA, Revu Patent:   WO2011/99033 A1, 2011 ;
  • Route2
    • In-stock
      (tert-Butoxycarbonyl)serine|CS-0166812
      3850-40-6
    • null|null
      100-46-9
    • ~%
    • In-stock
      (R)-tert-Butyl1-(benzylamino)-3-methoxy-1-oxopropan-2-ylcarbamate|CS-0006747
      880468-89-3

    References

    • Archimica GmbH Patent:   EP2399901 A1, 2011 ;
  • Route3
    • In-stock
      tert-Butyl (R)-(1-(benzylamino)-3-hydroxy-1-oxopropan-2-yl)carbamate|CS-0100204
      1253790-58-7
    • null|null
      77-78-1
    • ~77%
    • In-stock
      (R)-tert-Butyl1-(benzylamino)-3-methoxy-1-oxopropan-2-ylcarbamate|CS-0006747
      880468-89-3

    References

    • WISDOM, Richard; JUNG, Joerg; MEUDT, Andreas Patent: US2011/319649 A1, 2011 ; Location in patent: Page/Page column 5 ;

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-H332-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   76.66
  • LogP   1.8425
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   6

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