Carbamate Protective Groups

Carbamate Protective Groups

Overall Score5
  • Generality
  • Reagent Availability
  • Experimental User Friendliness
  • Criteria #4
  • Criteria #5
  • General Characteristics

In order to tame the basicity and the high reactivity of amines during multi-step synthesis, it is common to protect them with electron-withdrawing functional groups. Carbamate meets this need well in terms of generality and the convenience of protection/deprotection, better than amide and sulfonamide. Carbamate protection is essential in peptide synthesis and used regularly in all other situations as well.

  •  General References

  • Reaction Mechanism

  • Examples

Commonly used carbamates are listed below. Each has its own deprotection conditions, allowing for orthogonal strategies.

carbamate_protection_2.gif

  • Experimental Procedure

  • Experimental Tips

  • References

  • Related Books

[amazonjs asin=”0471697540″ locale=”US” title=”Greene’s Protective Groups in Organic Synthesis”]

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