19 11 Protection and Deprotection of Common Functional Groups Amines Alcohols For 1,2‐Diols For 1,3‐Diols For Phenols Protection and Deprotection for the Carboxylic Acid Group Protection and Deprotection of Carbonyl Group Protection and Deprotection of Terminal Alkyne References Alcohols Protection and Deprotection for the Carboxylic Acid Group Protection and Deprotection of Carbonyl Group Protection for the Terminal Alkyne CH
20 12 Amino Acids and Peptides Natural Amino Acids Nonnatural Amino Acids Solution‐Phase Peptide Synthesis Solid‐Phase Peptide Synthesis Cleavage Cocktail Cleavage Cocktail A Cleavage Cocktail B Reagents and conditions Covalent Peptides Staple Peptides Building Blocks for Stapled Peptides (Both L and D Analogs of Amino Acids Are Available) References
21
13 Functional Group Transformation
Alcohol to Aldehyde
Secondary Alcohol to Ketone
Primary Alcohol to Carboxylic Acid
1,2‐Diol Oxidation
Alcohol to Fluoride [11,14,15]
Alcohol to Chloride
Alcohol to Bromide
Alcohol to Iodide [13]
Alcohol to Ester
Alcohol to Ether
Alcohol to Sulfonic Ester
Alcohol to Methylene
Alcohol to Azide
Azide to Amine
Aldehyde to Alcohol
Aldehyde to Carboxylic Acid
Aldehyde to Difluoro [14, 15]
Ketone to Alcohol
Ketone to Ester
Ketone to Difluoro [14,15]
Ketone to Methylene
Ketone to Thioketone
Acid (Carboxylic) to Ester
Acid to Amide
Acid to Ketone
Ester to Acid
Ester to Aldehyde
Ester to Alcohol
Ester to Ketone
Nitro to Amine
Alkene to Epoxide
Alkene to Alkane
Alkyne to Alkane
Alkyne to Alkene
Cyano to Carboxylic Acid
Cyano to Amine [16]
Cyano to Amide
Methyl Phenyl Ether to Phenol [17, 18]
Toluene to Benzyl Halides
Alkylbenzene to Benzoic Acid
Aromatic Amine to Azide
Aromatic Halide to Aldehyde [21]
Aromatic Halide to Benzoic Acid [22]
Thioether