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Dimethyl 3,3'-disulfanediyl(2R,2'R)-bis(2-((tert-butoxycarbonyl)amino)propanoate)

  • CAS No. 77826-55-2

  • Cat. No. CS-0807980
  • Purity≥98%
  • MDL No.None

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

Dimethyl 3,3'-disulfanediyl(2R,2'R)-bis(2-((tert-butoxycarbonyl)amino)propanoate)|CS-0807980

Structure of 77826-55-2

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General Information

  • CAS No. 77826-55-2
  • Cat. No. CS-0807980
  • Purity ≥98%
  • MDL No. None
  • Storage RT, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₈H₃₂N₂O₈S₂
  • Molecular Weight 468.59
  • Synonym(s) None
  • SMILES O=C([C@H](CSSC[C@H](NC(OC(C)(C)C)=O)C(OC)=O)NC(OC(C)(C)C)=O)OC

Description

Dimethyl 3,3'-disulfanediyl(2R,2'R)-bis(2-((tert-butoxycarbonyl)amino)propanoate features a disulfide-linked backbone flanked by chiral proline-derived ester moieties. This configuration enables controlled disulfide bond formation in peptide synthesis and redox-sensitive conjugation strategies, offering robust stability under standard bench conditions while permitting selective reduction for downstream functionalization.

Application

Dimethyl 3,3'-disulfanediyl(2R,2'R)-bis(2-((tert-butoxycarbonyl)amino)propanoate serves as a bifunctional chiral building block for the synthesis of cysteine-derived peptides and thioether-linked scaffolds. The disulfide linkage enables controlled redox-dependent assembly, while the Boc-protected amines offer orthogonal handling and compatibility with standard peptide coupling protocols. Bench-stable and readily purified by chromatography, it facilitates efficient access to complex cysteine-containing architectures in medicinal chemistry and synthetic biology applications.

Safety Information

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GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P264-P280-P302+P352-P305+P351+P338-P362+P364

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Computational Chemistry Data

  • TPSA   129.26
  • LogP   2.5004
  • H_Acceptors   10
  • H_Donors   2
  • Rotatable_Bonds   9

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