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Benzyl(R)-(2,5-dioxopyrrolidin-3-yl)carbamate

  • CAS No. 179747-84-3

  • Cat. No. CS-0172726
  • Purity≥98%
  • MDL No.None

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

Benzyl(R)-(2,5-dioxopyrrolidin-3-yl)carbamate|CS-0172726

Structure of 179747-84-3

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General Information

  • CAS No. 179747-84-3
  • Cat. No. CS-0172726
  • Purity ≥98%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₂N₂O₄
  • Molecular Weight 248.23
  • Synonym(s) Carbamic acid, N-[(3R)-2,5-dioxo-3-pyrrolidinyl]-, phenylmethyl ester
  • SMILES O=C1[C@@H](CC(N1)=O)NC(OCC2=CC=CC=C2)=O

Description

Benzyl(R)-(2,5-dioxopyrrolidin-3-yl)carbamate serves as a chiral auxiliary in asymmetric synthesis, featuring a pyrrolidinone core that enables stereocontrolled functionalization. The benzyl carbamate group provides stable protection for amine intermediates under standard conditions, facilitating sequential transformations with minimal racemization. This structure combines robustness with precise spatial control, making it ideal for complex molecule assembly.

Application

Benzyl (R)-2,5-dioxopyrrolidin-3-yl carbamate serves as a robust chiral auxiliary in asymmetric synthesis, enabling stereoselective transformations via its stable pyrrolidine scaffold. The carbamate group facilitates easy handling and purification, while the benzyl protecting group ensures orthogonal deprotection under mild conditions. This compound functions effectively in enantioselective alkylation and conjugate addition reactions, offering high diastereoselectivity and compatibility with diverse functional groups.

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-H317
Precautionary Statements : P261-P264-P270-P272-P280-P302+P352-P330-P362+P364-P501

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Computational Chemistry Data

  • TPSA   84.5
  • LogP   0.3279
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   3

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