Synthesis and utility of 2-halo-O(6)-(benzotriazol-1-yl)-functionalized purine nucleosides

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Abstract

An efficient synthesis of 2-halo-O(6)-(benzotriazol-1-yl)-substituted purine nucleosides has been accomplished via (benzotriazol-1-yloxy)tris(dimethylamino) phosphonium hexafluorophosphate (BOP)-mediated coupling and subsequent halogenation via diazotization of the 2-amino group of various protected guanosines and directly from guanosine itself. These products are amenable to substitution and coupling reactions in the 2- and 6-positions and, accordingly, provide efficient access to highly functionalized purine nucleosides.
Original languageEnglish
Pages (from-to)1092 - 1098
Number of pages7
JournalEuropean Journal of Organic Chemistry
Volume2011
Issue number6
DOIs
Publication statusPublished - 2011

Cite this

@article{e0a1c68ed7de4b3f8289d7b89c0e40bc,
title = "Synthesis and utility of 2-halo-O(6)-(benzotriazol-1-yl)-functionalized purine nucleosides",
abstract = "An efficient synthesis of 2-halo-O(6)-(benzotriazol-1-yl)-substituted purine nucleosides has been accomplished via (benzotriazol-1-yloxy)tris(dimethylamino) phosphonium hexafluorophosphate (BOP)-mediated coupling and subsequent halogenation via diazotization of the 2-amino group of various protected guanosines and directly from guanosine itself. These products are amenable to substitution and coupling reactions in the 2- and 6-positions and, accordingly, provide efficient access to highly functionalized purine nucleosides.",
author = "Shane Devine and Peter Scammells",
year = "2011",
doi = "10.1002/ejoc.201001395",
language = "English",
volume = "2011",
pages = "1092 -- 1098",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-Blackwell",
number = "6",

}

Synthesis and utility of 2-halo-O(6)-(benzotriazol-1-yl)-functionalized purine nucleosides. / Devine, Shane; Scammells, Peter.

In: European Journal of Organic Chemistry, Vol. 2011, No. 6, 2011, p. 1092 - 1098.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Synthesis and utility of 2-halo-O(6)-(benzotriazol-1-yl)-functionalized purine nucleosides

AU - Devine, Shane

AU - Scammells, Peter

PY - 2011

Y1 - 2011

N2 - An efficient synthesis of 2-halo-O(6)-(benzotriazol-1-yl)-substituted purine nucleosides has been accomplished via (benzotriazol-1-yloxy)tris(dimethylamino) phosphonium hexafluorophosphate (BOP)-mediated coupling and subsequent halogenation via diazotization of the 2-amino group of various protected guanosines and directly from guanosine itself. These products are amenable to substitution and coupling reactions in the 2- and 6-positions and, accordingly, provide efficient access to highly functionalized purine nucleosides.

AB - An efficient synthesis of 2-halo-O(6)-(benzotriazol-1-yl)-substituted purine nucleosides has been accomplished via (benzotriazol-1-yloxy)tris(dimethylamino) phosphonium hexafluorophosphate (BOP)-mediated coupling and subsequent halogenation via diazotization of the 2-amino group of various protected guanosines and directly from guanosine itself. These products are amenable to substitution and coupling reactions in the 2- and 6-positions and, accordingly, provide efficient access to highly functionalized purine nucleosides.

UR - http://onlinelibrary.wiley.com.ezproxy.lib.monash.edu.au/doi/10.1002/ejoc.201001395/pdf

U2 - 10.1002/ejoc.201001395

DO - 10.1002/ejoc.201001395

M3 - Article

VL - 2011

SP - 1092

EP - 1098

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 6

ER -