Literature DB >> 14649900

A novel method for the synthesis of 4'-thiopyrimidine nucleosides using hypervalent iodine compounds.

Naozumi Nishizono1, Ryosuke Baba, Chika Nakamura, Kazuaki Oda, Minoru Machida.   

Abstract

The coupling reactions of cyclic sulfides with a silylated pyrimidine nucleobase using a hypervalent iodine reagent were investigated. The reaction of silylated uracil with cyclic sulfide 12 using PhI=O gave the desired beta-anomer 14 in moderate yield. 4'-Thiouridine (22) was obtained by deprotection of 14.

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Year:  2003        PMID： 14649900     DOI： 10.1039/b305644a

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  3 in total

1.  When nucleoside chemistry met hypervalent iodine reagents.

Authors:  Mahesh K Lakshman; Barbara Zajc
Journal:  ARKIVOC       Date:  2017-12-21       Impact factor: 1.140

Review 2.  Glycosylation reactions mediated by hypervalent iodine: application to the synthesis of nucleosides and carbohydrates.

Authors:  Yuichi Yoshimura; Hideaki Wakamatsu; Yoshihiro Natori; Yukako Saito; Noriaki Minakawa
Journal:  Beilstein J Org Chem       Date:  2018-06-28       Impact factor: 2.883

3.  Synthesis of 4-Selenothreofuranose Derivatives via Pummerer-Type Reactions of trans-3,4-Dioxygenated Tetrahydroselenophenes Mediated by a Selenonium Intermediate.

Authors:  Michio Iwaoka; Yuta Hiyoshi; Shota Arai; Takeru Ito
Journal:  ACS Omega       Date:  2021-06-25
  3 in total

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