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tert-Butyl (R)-(1-cyclohexyl-2-hydroxyethyl)carbamate

  • CAS No. 188348-00-7

  • Cat. No. CS-0093774
  • Purity≥97%
  • MDL No.MFCD04112590

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

tert-Butyl (R)-(1-cyclohexyl-2-hydroxyethyl)carbamate|CS-0093774

Structure of 188348-00-7

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General Information

  • CAS No. 188348-00-7
  • Cat. No. CS-0093774
  • Purity ≥97%
  • MDL No. MFCD04112590
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₂₅NO₃
  • Molecular Weight 243.34
  • Synonym(s) tert-butyl N-[(1R)-1-cyclohexyl-2-hydroxy-ethyl]carbamate
  • SMILES OC[C@H](NC(OC(C)(C)C)=O)C1CCCCC1

Description

This chiral carbamate features a tert-butyl-protected hydroxyl group and a cyclohexyl-substituted ethyl scaffold, enabling straightforward deprotection under mild acidic conditions. The (R)-configuration provides stereochemical fidelity in asymmetric synthesis, while the bench-stable, moisture-tolerant nature simplifies handling in multi-step workflows.

Application

tert-Butyl (R)-(1-cyclohexyl-2-hydroxyethyl)carbamate serves as a chiral auxiliary and protected amino alcohol synthon, enabling stereoselective transformations in asymmetric synthesis. The tert-butyl carbamate group provides robust protection for primary amines, while the hydroxyl functionality supports orthogonal derivatization. Its bench-stable nature and compatibility with standard coupling and reduction protocols make it a practical building block for complex molecule assembly.

Synthesis

  • Route1

    References

    • Tucci, Fabio C.; Zhu, Yun-Fei; Guo, Zhiqiang; Gross, Timothy D.; Connors Jr., Patrick J.; Gao, Yinghong; Rowbottom, Martin W.; Struthers, R. Scott; Reinhart, Greg J.; Xie, Qiu; Chen, Ta Kung; Bozigian, Haig; Bonneville, Anne L. Killam; Fisher, Andrew; Jin, Liping; Saunders, John; Chen, Chen Journal of Medicinal Chemistry, 2004 , vol. 47, # 14 p. 3483 - 3486
  • Route2
    • null|null
      849178-88-7
    • ~65%
    • In-stock
      tert-Butyl (R)-(1-cyclohexyl-2-hydroxyethyl)carbamate|CS-0093774
      188348-00-7

    References

    • Ko, Chang Hong; Jung, Doo Young; Kim, Min Kyun; Kim, Yong Hae Synlett, 2005 , # 2 art. no. U27404ST, p. 304 - 308
  • Route3
    • null|null
      188348-02-9
    • ~84%
    • In-stock
      tert-Butyl (R)-(1-cyclohexyl-2-hydroxyethyl)carbamate|CS-0093774
      188348-00-7

    References

    • Kiyoi, Takao; York, Mark; Francis, Stuart; Edwards, Darren; Walker, Glenn; Houghton, Andrea K.; Cottney, Jean E.; Baker, James; Adam, Julia M. Bioorganic and Medicinal Chemistry Letters, 2010 , vol. 20, # 16 p. 4918 - 4921

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07,GHS09
Signal Word : Warning
UN#: 3077
Class : 9
Packing Group : Ⅲ
Hazard Statements : H302-H315-H319-H335-H410
Precautionary Statements : P261-P264-P270-P271-P273-P280-P302+P352-P304+P340-P330-P362+P364-P391-P405-P501

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Computational Chemistry Data

  • TPSA   58.56
  • LogP   2.4523
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   3

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