A simple and efficient method for synthesis of 5-substituted 2’-deoxyuridine nucleosides using metal–halogen exchange reaction of 5-iodo-2’-deoxyuridine sodium salt

Mariko Aso, Toshiyuki Kaneko, Morihide Nakamura, Noboru Koga, Hiroshi Suemune

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Treatment of the sodium salt of 2’-deoxy-3’, 5’-bis-O-(tert-butyldimethylsilyl)-5-iodouridine (3) with n-BuLi effected regioselective lithiation at the 5-position and the following reaction with various electrophiles afforded 5-substituted 2’-deoxyuridines including 1b, the precursor of stable spin-labeled 1a, in good yields.

Original languageEnglish
Pages (from-to)1094-1095
Number of pages2
JournalChemical Communications
Volume3
Issue number9
DOIs
Publication statusPublished - Jan 1 2003

Fingerprint

Deoxyuridine
Nucleosides
Salts
Sodium
n-butyllithium
5-iodouridine

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

Cite this

A simple and efficient method for synthesis of 5-substituted 2’-deoxyuridine nucleosides using metal–halogen exchange reaction of 5-iodo-2’-deoxyuridine sodium salt. / Aso, Mariko; Kaneko, Toshiyuki; Nakamura, Morihide; Koga, Noboru; Suemune, Hiroshi.

In: Chemical Communications, Vol. 3, No. 9, 01.01.2003, p. 1094-1095.

Research output: Contribution to journalArticle

@article{939179b2d8c0426393d2b610833cf168,
title = "A simple and efficient method for synthesis of 5-substituted 2’-deoxyuridine nucleosides using metal–halogen exchange reaction of 5-iodo-2’-deoxyuridine sodium salt",
abstract = "Treatment of the sodium salt of 2’-deoxy-3’, 5’-bis-O-(tert-butyldimethylsilyl)-5-iodouridine (3) with n-BuLi effected regioselective lithiation at the 5-position and the following reaction with various electrophiles afforded 5-substituted 2’-deoxyuridines including 1b, the precursor of stable spin-labeled 1a, in good yields.",
author = "Mariko Aso and Toshiyuki Kaneko and Morihide Nakamura and Noboru Koga and Hiroshi Suemune",
year = "2003",
month = "1",
day = "1",
doi = "10.1039/b301425h",
language = "English",
volume = "3",
pages = "1094--1095",
journal = "Chemical Communications",
issn = "1359-7345",
publisher = "Royal Society of Chemistry",
number = "9",

}

TY - JOUR

T1 - A simple and efficient method for synthesis of 5-substituted 2’-deoxyuridine nucleosides using metal–halogen exchange reaction of 5-iodo-2’-deoxyuridine sodium salt

AU - Aso, Mariko

AU - Kaneko, Toshiyuki

AU - Nakamura, Morihide

AU - Koga, Noboru

AU - Suemune, Hiroshi

PY - 2003/1/1

Y1 - 2003/1/1

N2 - Treatment of the sodium salt of 2’-deoxy-3’, 5’-bis-O-(tert-butyldimethylsilyl)-5-iodouridine (3) with n-BuLi effected regioselective lithiation at the 5-position and the following reaction with various electrophiles afforded 5-substituted 2’-deoxyuridines including 1b, the precursor of stable spin-labeled 1a, in good yields.

AB - Treatment of the sodium salt of 2’-deoxy-3’, 5’-bis-O-(tert-butyldimethylsilyl)-5-iodouridine (3) with n-BuLi effected regioselective lithiation at the 5-position and the following reaction with various electrophiles afforded 5-substituted 2’-deoxyuridines including 1b, the precursor of stable spin-labeled 1a, in good yields.

UR - http://www.scopus.com/inward/record.url?scp=0038028217&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0038028217&partnerID=8YFLogxK

U2 - 10.1039/b301425h

DO - 10.1039/b301425h

M3 - Article

AN - SCOPUS:0038028217

VL - 3

SP - 1094

EP - 1095

JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

IS - 9

ER -