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tert-Butyl (S)-(1-hydroxypent-4-en-2-yl)carbamate

  • CAS No. 116613-81-1

  • Cat. No. CS-0133771
  • Purity≥97%
  • MDL No.MFCD29042783

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

tert-Butyl (S)-(1-hydroxypent-4-en-2-yl)carbamate|CS-0133771

Structure of 116613-81-1

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General Information

  • CAS No. 116613-81-1
  • Cat. No. CS-0133771
  • Purity ≥97%
  • MDL No. MFCD29042783
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₉NO₃
  • Molecular Weight 201.26
  • Synonym(s) Carbamic acid, N-[(1S)-1-(hydroxymethyl)-3-buten-1-yl]-, 1,1-dimethylethyl ester
  • SMILES C=CC[C@H](NC(OC(C)(C)C)=O)CO

Description

This chiral carbamate features a tert-butyl-protected amine tethered to a hydroxypentenyl scaffold, enabling straightforward deprotection and functionalization. The allylic alcohol moiety supports stereoselective transformations, while the bulky tert-butyl group enhances stability and facilitates purification. Ideal for asymmetric synthesis and peptide coupling applications.

Application

tert-Butyl (S)-(1-hydroxypent-4-en-2-yl)carbamate serves as a versatile chiral building block for asymmetric synthesis, enabling efficient access to functionalized pyrrolidines and other nitrogen-containing heterocycles. The pendant hydroxyl group facilitates selective derivatization, while the terminal alkene supports downstream transformations such as olefin metathesis or epoxidation. Its bench-stable tert-butyl carbamate (Boc) protection ensures compatibility with standard peptide coupling conditions and broad functional group tolerance, making it well-suited for iterative synthetic sequences in medicinal chemistry and process development.

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 : H302-H315-H319-H335
Precautionary Statements : P261-P280-P302+P352

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Computational Chemistry Data

  • TPSA   58.56
  • LogP   1.4481
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   4

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