Synthesis of the 3′-C-hydroxymethyl-branched locked nucleic acid thymidine monomer

Surender Kumar, Pawan K. Sharma, Paul C. Stein, Poul Nielsen*

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Abstrakt

A 3′-C-hydroxymethyl-branched Locked Nucleic Acid (LNA) monomer 3 was synthesized from diacetone-α-D-glucose taking advantage of a stereoselective Grignard reaction for the introduction of a vinyl group, an aldol/Cannizzarro sequence for introducing the 4′-substituent, oxidative cleavage of the vinyl group using a RuO4-based protocol, Vorbrüggen-type nucleobase coupling and finally the ring closure by ether formation giving the bicyclic skeleton.

OriginalsprogEngelsk
TidsskriftEuropean Journal of Organic Chemistry
Vol/bind2008
Udgave nummer34
Sider (fra-til)5715-5722
Antal sider8
ISSN1434-193X
DOI
StatusUdgivet - 2008

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