5. Protecting Groups

Description

Chemistry Flashcards on 5. Protecting Groups, created by John Rivada on 20/04/2019.
John Rivada
Flashcards by John Rivada, updated more than 1 year ago
John Rivada
Created by John Rivada over 5 years ago
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Resource summary

Question Answer
Properties for kinetic product -Forms faster -Rx usually short -Low temperature -Reversible under thermodynamic conditions
Properties for thermodynamic product -Forms more slowly but more stable -Rx is long -High temperature -Irreversible
Mechanism?
Mechanism?
How do you protect the amine group of an amino acid? Cbz Benzyl chloroformate
How do you protect the amine group of an amino acid? Boc (t-BuOCO) Deprotect with H+ and H2O
How do you protect the amine group of an amino acid? FMoc-Cl, base Deprotect with amine base (e.g. pyridine)
How to make t-butyl ester **
How do you protect the carboxylic acid group of an amino acid? ROH, H+ Deprotect with -OH (LiOH, NaOH)
How do you protect the carboxylic acid group of an amino acid? isobutene, H+ Deprotect with strong acid
How do you protect the carboxylic acid group of an amino acid? PHCH2OH and H+ or PhCH2Br and base Deprotect with H2 + cat. Pd/C or -OH
Slide 27 **
Slide 29 **
Slide 30 **
Solid phase peptide synthesis 88
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