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Synthesis of (Purin-6-yl)methylphosphonate Bases and Nucleosides

SYSNO ASEP	0342810
Document Type	J - Journal Article
R&D Document Type	Journal Article
Subsidiary J	Článek ve WOS
Title	Synthesis of (Purin-6-yl)methylphosphonate Bases and Nucleosides
Author(s)	Hasník, Zbyněk (UOCHB-X) Pohl, Radek (UOCHB-X)_{RID, ORCID} Hocek, Michal (UOCHB-X)_{RID, ORCID}
Number of authors	3
Source Title	Tetrahedron Letters. - : Elsevier - ISSN 0040-4039 Roč. 51, č. 18 (2010), s. 2464-2466
Number of pages	3 s.
Language	eng - English
Country	GB - United Kingdom
Keywords	purines ; nucleosides ; phosphonates ; cross-coupling
Subject RIV	CC - Organic Chemistry
R&D Projects	1M0508 GA MŠMT - Ministry of Education, Youth and Sports (MEYS)
CEZ	AV0Z40550506 - UOCHB-X (2005-2011)
UT WOS	000276972200021
DOI	10.1016/j.tetlet.2010.02.167
Annotation	Three approaches to the synthesis of the title (purin-6-yl)methylphosphonates were investigated and compared. While, the Arbuzov reaction of 6-(iodomethyl)purines with triethyl phosphite did not work, Michaelis–Becker alkylation of the sodium salt of diethyl phosphonate with 6-(mesyloxymethyl)purines gave the desired products in good yields. The best method was based on Rh- or Pd-catalyzed cross-coupling reactions of 6-iodopurines with (diisopropoxyphosphorylmethyl)zinc bromide.
Workplace	Institute of Organic Chemistry and Biochemistry
Contact	asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434
Year of Publishing	2011

Number of the records: 1