Nucleobase protection with allyloxycarbonyl

Area of Science:

• Organic Chemistry
• Nucleoside Chemistry
• Oligonucleotide Synthesis

Background:

• Protected nucleosides are crucial for oligonucleotide synthesis.
• Existing methods may lack stability or require harsh deprotection conditions.

Purpose of the Study:

• To describe protocols for preparing N-allyloxycarbonyl-protected 5'-O-(4,4'-dimethoxytrityl)-2'-deoxyribonucleosides and 2'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)ribonucleosides.
• To provide versatile building blocks for natural and artificial oligonucleotide synthesis.

Main Methods:

• Preparation of N-allyloxycarbonyl-protected deoxyribonucleosides.
• Preparation of 2'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)ribonucleosides.
• Assessment of protecting group stability during phosphoramidite conversion and oligonucleotide synthesis.

Main Results:

• Established protocols for key protected nucleoside building blocks.
• Demonstrated stability of protected nucleosides under synthesis conditions.
• Confirmed facile and clean removal of N-allyloxycarbonyl group via organopalladium catalysis.

Conclusions:

• The described protected nucleosides are stable and versatile for oligonucleotide synthesis.
• The N-allyloxycarbonyl protecting group enables mild deprotection, suitable for sensitive modifications.
• These building blocks facilitate the creation of diverse natural and artificial oligonucleotides.