Synthesis and testing of new modified nucleosides

Area of Science:

• Organic Chemistry
• Medicinal Chemistry
• Nucleoside Analog Synthesis

Background:

• Modified nucleosides are crucial in antiviral and anticancer therapies.
• Existing synthetic routes often lack efficiency or broad applicability.
• Development of enantiomerically pure nucleoside analogs is essential for targeted drug design.

Purpose of the Study:

• To establish novel, high-yielding synthetic pathways for diverse modified nucleosides.
• To synthesize specific classes of isonucleosides, including methylene-expanded and dideoxy analogs.
• To prepare enantiomerically pure L-ribose and 2-deoxy-L-ribose derivatives and their corresponding nucleosides.

Main Methods:

• Development of new synthetic methodologies for nucleoside analog construction.
• Stereoselective synthesis to obtain both D- and L-enantiomers.
• Preparation of oxa and thia analogues of dideoxy isonucleosides.

Main Results:

• Successfully synthesized D- and L-enantiomers of methylene-expanded oxetanocin isonucleosides (1a-c).
• Prepared L-2',3'-dideoxy isonucleosides (2abc), including oxa and thia variants.
• Established new routes for L-ribose (3a) and 2-deoxy-L-ribose (3b), and their modified nucleosides (4).

Conclusions:

• The developed routes offer efficient and high-yielding access to valuable modified nucleosides.
• This work expands the toolkit for synthesizing enantiomerically pure nucleoside analogs.
• The synthesized compounds hold potential for further investigation in medicinal chemistry.