Literature DB >> 15049678

Preparative and stereoselective synthesis of the versatile intermediate for carbocyclic nucleosides: effects of the bulky protecting groups to enforce facial selectivity.

Won Jun Choi1, Hyung Ryong Moon, Hea Ok Kim, Byul Nae Yoo, Jeong A Lee, Dae Hong Shin, Lak Shin Jeong.   

Abstract

The preparative and stereoselective synthesis (45-50% overall yields) of the target compound 17 has been accomplished from D-ribose. The bulky protecting groups such as TBDPS and Trityl enforced the facial selectivity during Grignard reaction to give the tertiary beta-allylic alcohol 16 as the sole product, which was oxidatively rearranged to the key molecule 17 in excellent yield.

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Year:  2004        PMID： 15049678     DOI： 10.1021/jo0356762

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


  10 in total

1.  Methanocarba ring as a ribose modification in ligands of G protein-coupled purine and pyrimidine receptors: synthetic approaches.

Authors:  Dilip K Tosh; Kenneth A Jacobson
Journal:  Medchemcomm       Date:  2013-12-17       Impact factor: 3.597

2.  A greener enantioselective synthesis of the antiviral agent North-methanocarbathymidine (N-MCT) from 2-deoxy-d-ribose.

Authors:  Olaf R Ludek; Victor E Marquez
Journal:  Tetrahedron       Date:  2009-10-10       Impact factor: 2.457

Review 3.  Polypharmacology of conformationally locked methanocarba nucleosides.

Authors:  Kenneth A Jacobson; Dilip K Tosh; Kiran S Toti; Antonella Ciancetta
Journal:  Drug Discov Today       Date:  2017-08-03       Impact factor: 7.851

4.  Efficient, large-scale synthesis and preclinical studies of MRS5698, a highly selective A3 adenosine receptor agonist that protects against chronic neuropathic pain.

Authors:  Dilip K Tosh; Janak Padia; Daniela Salvemini; Kenneth A Jacobson
Journal:  Purinergic Signal       Date:  2015-06-27       Impact factor: 3.765

5.  6'-Oxa Analogs of S-Adenosylhomocysteine.

Authors:  Weikuan Li; Wei Ye; Stewart W Schneller
Journal:  Tetrahedron       Date:  2012-01-07       Impact factor: 2.457

6.  Rigidified A3 Adenosine Receptor Agonists: 1-Deazaadenine Modification Maintains High in Vivo Efficacy.

Authors:  Dilip K Tosh; Steven Crane; Zhoumou Chen; Silvia Paoletta; Zhan-Guo Gao; Elizabeth Gizewski; John A Auchampach; Daniela Salvemini; Kenneth A Jacobson
Journal:  ACS Med Chem Lett       Date:  2015-05-20       Impact factor: 4.345

Review 7.  Expanding the repertoire of methanocarba nucleosides from purinergic signaling to diverse targets.

Authors:  Kenneth A Jacobson; Veronica Salmaso; R Rama Suresh; Dilip K Tosh
Journal:  RSC Med Chem       Date:  2021-07-13

Review 8.  Recent Advances in the Chemical Synthesis and Evaluation of Anticancer Nucleoside Analogues.

Authors:  Mieke Guinan; Caecilie Benckendorff; Mark Smith; Gavin J Miller
Journal:  Molecules       Date:  2020-04-28       Impact factor: 4.411

9.  Enhancing the Antiviral Efficacy of RNA-Dependent RNA Polymerase Inhibition by Combination with Modulators of Pyrimidine Metabolism.

Authors:  Qi Liu; Amita Gupta; Ayse Okesli-Armlovich; Wenjie Qiao; Curt R Fischer; Mark Smith; Jan E Carette; Michael C Bassik; Chaitan Khosla
Journal:  Cell Chem Biol       Date:  2020-05-21       Impact factor: 8.116

10.  A further contribution to the study of sagittamide A: synthesis of a pivotal intermediate belonging to a rare L-series.

Authors:  Anne Humbert; Karen Plé; Dominique Harakat; Agathe Martinez; Arnaud Haudrechy
Journal:  Molecules       Date:  2012-06-25       Impact factor: 4.411
  10 in total

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