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How to remove acetonide?

How to remove acetonide?

Acetonide is a common protecting group for 1,2- and 1,3-diols. The protecting group can be removed by hydrolysis of the ketal using dilute aqueous acid.

How can we protect diols?

The most important method for the protection 1.2 diols or 1,3 diols is to convert them into a cyclic acetals or ketals. When the alcohols do not carry base labile group, they can be converted into their methyl ethers with suitable methylating agents i.e. diazomethane, methyl iodide etc.

How do you Deprotect acetals?

Deprotection of acetals and ketals can be achieved by using a catalytic amount of sodium tetrakis(3,5-trifluoromethylphenyl)borate (NaBArF4) in water at 30 °C. For example, a quantitative conversion of 2-phenyl-1,3-dioxolane into benzaldehyde was accomplished within five minutes.

How to protect primary amines?

The most popular choice of protecting group for amine nitrogen is the carbamate functional group….The nitrogen of a carbamate is relatively non-nucleophilic, and furthermore, carbamates are:

  1. easily installed on nitrogen.
  2. inert to a wide variety of reaction conditions.
  3. easily removed without affecting existing amide groups.

How is dopamine protected by acetonide ( 3 ) 22?

Acetonide-protected dopamine (3) 22 was obtained by deprotection of the phthaloyl group of 2 with hydrazine in DCM.

Which is acetonide derivatives furnish the deprotected diols?

Various acetonide derivatives furnish the corresponding deprotected diols in good yields, while a large number of acid labile protecting functional groups and other functional moieties were found to be unaffected under the conditions. M. R. Maddani, K. R. Prabhu, Synlett, 2011, 821-825.

Which is the best reagent for terminal acetonide deprotection?

Aqueous tert -butyl hydroperoxide (70%) is an inexpensive reagent for the regioselective and chemoselective deprotection of terminal acetonide groups.

How is the deprotection of acetals and ketals achieved?

Deprotection of acetals and ketals can be achieved by using a catalytic amount of sodium tetrakis (3,5-trifluoromethylphenyl)borate (NaBArF 4) in water at 30 °C. For example, a quantitative conversion of 2-phenyl-1,3-dioxolane into benzaldehyde was accomplished within five minutes. C.-C. Chang, B.-S. Liao, S.-T. Liu, Synlett, 2007, 283-287.