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(S)-Benzyl (2-oxotetrahydrofuran-3-yl)carbamate

  • CAS No. 35677-89-5

  • Cat. No. CS-W012893
  • Purity≥98%
  • MDL No.MFCD00674555

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

(S)-Benzyl (2-oxotetrahydrofuran-3-yl)carbamate|CS-W012893

Structure of 35677-89-5

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General Information

  • CAS No. 35677-89-5
  • Cat. No. CS-W012893
  • Purity ≥98%
  • MDL No. MFCD00674555
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₃NO₄
  • Molecular Weight 235.24
  • Synonym(s) N-Z-L-homoserine lactone
  • SMILES O=C1[C@@H](NC(OCC2=CC=CC=C2)=O)CCO1

Description

This chiral building block features a (S)-configured benzyl carbamate tethered to a 2-oxotetrahydrofuran-3-yl moiety, offering high stereocontrol in asymmetric synthesis. The oxo group enhances reactivity for downstream functionalization, while the carbamate handle enables selective protection and cleavage under mild conditions.

Application

(S)-Benzyl (2-oxotetrahydrofuran-3-yl)carbamate serves as a chiral building block for the synthesis of tetrahydrofuran-containing pharmaceuticals and natural products. Its functionality enables straightforward access to enantiopure heterocycles via reductive amination, nucleophilic addition, or ring-opening reactions. The carbamate group provides stability and facilitates purification, while the oxo substituent offers a handle for further functionalization. This compound is bench-stable and compatible with standard synthetic workflows.

Synthesis

  • Route1
    • null|null
      501-53-1
    • ~%
    • In-stock
      (S)-Benzyl (2-oxotetrahydrofuran-3-yl)carbamate|CS-W012893
      35677-89-5

    References

    • Journal of Organic Chemistry, , vol. 68, # 1 p. 50 - 54
  • Route2

    References

    • Ozinskas; Rosenthal Journal of Organic Chemistry, 1986 , vol. 51, # 26 p. 5047 - 5050
  • Route3
    • (S)-tert-Butyl 2-(((benzyloxy)carbonyl)amino)-4-hydroxybutanoate|CS-0312346
      78266-81-6
    • ~90%
    • In-stock
      (S)-Benzyl (2-oxotetrahydrofuran-3-yl)carbamate|CS-W012893
      35677-89-5

    References

    • Easmon; Heinisch; Holzer; Matuszczak Archiv der Pharmazie, 1995 , vol. 328, # 4 p. 367 - 370

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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   64.63
  • LogP   1.2283
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   3

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