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Literature DB >> 23806030

Synthesis of 2'-deoxy-9-deaza nucleosides using Heck methodology.

Kartik Temburnikar¹, Kelin Brace, Katherine L Seley-Radtke.

Abstract

During the synthesis of a series of 2'-deoxy-9-deaza nucleosides using Heck methodology, the necessity for a pyrrole protecting group was discovered. The results of this brief study revealed that the benzyloxymethyl (BOM) group proved optimal, and Heck coupling using Jeffery conditions increased the coupling yield significantly. The results are reported herein.

Entities: Chemical Disease Gene Species

Mesh：

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Year: 2013 PMID： 23806030 PMCID： PMC5638437 DOI： 10.1021/jo400913k

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

22 in total

1. Synthesis and biological evaluation of 2- and 7-substituted 9-deazaadenosine analogues.

Authors: Mao-Chin Liu; Mei-Zhen Luo; Diane E Mozdziesz; Alan C Sartorelli
Journal: Nucleosides Nucleotides Nucleic Acids Date: 2005 Impact factor: 1.381

Review 2. A review: synthesis of aryl C-glycosides via the heck coupling reaction.

Authors: Kevin W Wellington; Steven A Benner
Journal: Nucleosides Nucleotides Nucleic Acids Date: 2006 Impact factor: 1.381

3. pH-Independent triplex formation: hairpin DNA containing isoguanine or 9-deaza-9-propynylguanine in place of protonated cytosine.

Authors: Frank Seela; Khalil I Shaikh
Journal: Org Biomol Chem Date: 2006-10-02 Impact factor: 3.876

4. Addition of lithiated 9-deazapurine derivatives to a carbohydrate cyclic imine: convergent synthesis of the aza-C-nucleoside immucillins.

Authors: G B Evans; R H Furneaux; T L Hutchison; H S Kezar; P E Morris; V L Schramm; P C Tyler
Journal: J Org Chem Date: 2001-08-24 Impact factor: 4.354

Synthesis of 2'-deoxy-9-deaza nucleosides using Heck methodology.

1. Synthesis and biological evaluation of 2- and 7-substituted 9-deazaadenosine analogues.

Review 2. A review: synthesis of aryl C-glycosides via the heck coupling reaction.

3. pH-Independent triplex formation: hairpin DNA containing isoguanine or 9-deaza-9-propynylguanine in place of protonated cytosine.

4. Addition of lithiated 9-deazapurine derivatives to a carbohydrate cyclic imine: convergent synthesis of the aza-C-nucleoside immucillins.

5. Tricyclic 2'-C-modified nucleosides as potential anti-HCV therapeutics.

6. Synthesis of tert-butoxycarbonyl (Boc)-protected purines.

7. Synthesis and antitumor activity of thieno-separated tricyclic purines.

8. Modular and practical synthesis of 6-substituted pyridin-3-yl C-nucleosides.

Review 9. Enzymology of purine and pyrimidine antimetabolites used in the treatment of cancer.

10. Hetero-expanded purine nucleosides. Design, synthesis and preliminary biological activity.

1. Antiproliferative activities of halogenated thieno[3,2-d]pyrimidines.

2. Antiproliferative activities of halogenated pyrrolo[3,2-d]pyrimidines.