Synthesis of the 3′‐ C ‐Hydroxymethyl‐Branched Locked Nucleic Acid Thymidine Monomer | Zendy

Kumar Surender | Zendy; Sharma Pawan K. | Zendy; Stein Paul C. | Zendy; Nielsen Poul | Zendy

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Synthesis of the 3′‐ C ‐Hydroxymethyl‐Branched Locked Nucleic Acid Thymidine Monomer

Author(s) -

Kumar Surender,

Sharma Pawan K.,

Stein Paul C.,

Nielsen Poul

Publication year - 2008

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200800716

Subject(s) - chemistry , nucleic acid , hydroxymethyl , stereochemistry , monomer , substituent , stereoselectivity , aldol reaction , furan , nucleobase , furanose , thymidine , protecting group , nucleic acid analogue , ring (chemistry) , dna , organic chemistry , catalysis , biochemistry , alkyl , nucleic acid thermodynamics , base sequence , polymer

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 RuO 4 ‐based protocol, Vorbrüggen‐type nucleobase coupling and finally the ring closure by ether formation giving the bicyclic skeleton. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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