Protecting Groups Flashcards
What is a THP group?
(THP ethers are stable to hydrogenation, strong bases, hydrides, fluorides, oxidants - needs a mild acid to remove)
What do you react with following alcohol with to add a THP ether protecting group?
React with DHP and acid catalyst
What is the mechansim for protecting an alcohol using THP ethers
How do we deprotect an alcohol from a THP ether?
React with 2M HCl (aq) and THF
What do you react with the following alcohol to form a benzyl ether protecting group?
- React with BnBr
- Stable to: strong base, hydride, fluoride, oxidants
How do we remove the following benzyl ether protecting group from an alcohol?
- Through hydrogenation or HBr/AcOH
How would you react the following diol to add a acetonide protecting group?
- Stable to: hydrogenation, strong base, hydride, fluoride, oxidants
How do we remove the acetonide protecting group from this alcohol?
- Mild aqueous acid
How would you react the following diol to add a silane protecting group
Stable to: strong bases, hydrides, hydrogenation, oxidants
How do we remove this silane protecting group from the alcohol?
Remove by: TBAF or 2M HCl
How would we react the following ketone/aldehyde to add a dioxolane protecting group
Stable to: hydrogenation, strong base, hydrides, fluoride, oxidants
How do we remove the dioxolane protecting group to reform the ketone/aldehyde
mild aqueous acid
How would we react the following carboxylic acid to add a methyl protecting group?
Stable to: base, mild acid and F⁻
How would we remove the methyl protecting group from the carboxylic acid
React with sodium hydroxide base
How would we react the following carboxylic acid to add a benzyl protecting group?
Stable to base, mild acid, F⁻
How would we remove the benzyl protecting group from the carboxylic acid?
React with hydrogen and palladium catalyst
How would we react the following carboxylic acid to add a tert-butyl ester protecting group?
Stable to: OH⁻, Nu, H₂, NaBH₄, F⁻
How would we remove the tert-Butyl ester protecting group from the carboxylic acid
What is the mechanism for the following reaction
How could we react the following amine to add a BOC carbamtes protecting group
Stable to: hydrogenation, strong bases, hydrides, fluoride and oxidants
How would we remove the following BOC carbamate protecting group from a amine
2M HCl or TFA
What is the mechanism for the deprotect of the amine from a BOC carbamate
How could we react the following amine to add a FMOC carbamate protecting group?
FMOC groups are stable to hydrogenation, acid, hydrides, fluoride and oxidants
How could we remove the following FMOC carbamate protecting group from the amine?
Piperidine
What is the mechanism for removing a FMOC carbamate protecing group from an amine?
How would we react an amine to add a Cbz Carbamate protecting group?
Stable to: strong base, hydrides, fluoride, oxidants and acids
How would we remove a Cbz Carbamate protecting group from an amine?
Removed by hydrogenation or HBr/AcOH
How would we react an amine to add a Tosylate protecting group (most protecting)
Stable to: strong bases, hydrides, fluoride, oxidants and acids
How would we remove a Tosylate protecting group from an amine?
Na/NH₃ - strongly reducing conditions
