Journal
TETRAHEDRON LETTERS
Volume 51, Issue 18, Pages 2464-2466Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.02.167
Keywords
Purines; Nucleosides; Phosphonates; Cross-coupling reactions
Categories
Funding
- Academy of Sciences of the Czech Republic [Z4 055 0506]
- Ministry of Education, Youth and Sports [1M0508]
- Gi-lead Sciences, Inc. (Foster City, CA, USA)
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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. In this way a small series of 6-(diisopropoxyphosphorylmethyl)purine bases and nucleosides was prepared in high yields. (C) 2010 Elsevier Ltd. All rights reserved.
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