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

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

*Corresponding author for this work

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

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.

Original languageEnglish
JournalEuropean Journal of Organic Chemistry
Volume2008
Issue number34
Pages (from-to)5715-5722
Number of pages8
ISSN1434-193X
DOIs
Publication statusPublished - 2008

Fingerprint

Ether
Thymidine
Monomers
Glucose
3-hydroxybutanal
locked nucleic acid

Keywords

  • Locked nucleic acid
  • Nucleosides
  • Oligonucleotides
  • Ruthenium oxidation

Cite this

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title = "Synthesis of the 3′-C-hydroxymethyl-branched locked nucleic acid thymidine monomer",
abstract = "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, Vorbr{\"u}ggen-type nucleobase coupling and finally the ring closure by ether formation giving the bicyclic skeleton.",
keywords = "Locked nucleic acid, Nucleosides, Oligonucleotides, Ruthenium oxidation",
author = "Surender Kumar and Sharma, {Pawan K.} and Stein, {Paul C.} and Poul Nielsen",
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pages = "5715--5722",
journal = "European Journal of Organic Chemistry",
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publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",
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Synthesis of the 3′-C-hydroxymethyl-branched locked nucleic acid thymidine monomer. / Kumar, Surender; Sharma, Pawan K.; Stein, Paul C.; Nielsen, Poul.

In: European Journal of Organic Chemistry, Vol. 2008, No. 34, 2008, p. 5715-5722.

Research output: Contribution to journalJournal articleResearchpeer-review

TY - JOUR

T1 - Synthesis of the 3′-C-hydroxymethyl-branched locked nucleic acid thymidine monomer

AU - Kumar, Surender

AU - Sharma, Pawan K.

AU - Stein, Paul C.

AU - Nielsen, Poul

PY - 2008

Y1 - 2008

N2 - 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.

AB - 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.

KW - Locked nucleic acid

KW - Nucleosides

KW - Oligonucleotides

KW - Ruthenium oxidation

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DO - 10.1002/ejoc.200800716

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JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

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