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Volume 2012, Issue 1
  • EISSN: 2223-506X

Abstract

Abstract

: Attempts to optimize the synthetic yield of known macrocyclic phosphonates resulted in the discovery of two new macrocyclic bisphosphonate dimers. : An attempt was carried out to optimize the yield of a known macrocyclic bisphosphonate dimer, , over the yield of monomers and , using the Mitsunobu protocol in the macrocyclization step. Cyclization reactions were carried out at 0.003 M, 0.004 M, 0.005 M, 0.008 M and 0.02 M, compared to 0.002 M in our initial report of the synthesis of monomers. : In this attempt to optimize the production of dimer , two new macrocyclic diastereomers of , namely 28-membered bisphosphonates and , were isolated in yields of 3% and 2%, respectively, and characterized by FTIR, LC-MS, , and NMR as well as by X-ray crystallography. : The results described herein further illustrate the utility of the Mitsunobu macrocyclization (ring-closing) reaction toward the synthesis of macrocyclic phosphonates. The X-ray crystallographic characterization of the three bisphosphonate dimers, together with correlations to specific and NMR resonances allowed for the assignments of relative stereochemistries between the various dimers.

© 2012 Patrick, Yeh, Comba, Everett, Koczkur & Pungente, licensee Bloomsbury Qatar Foundation Journals.
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2012-09-20
2024-11-13
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/content/journals/10.5339/connect.2012.10
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Synthesis and characterization of macrocyclic bisphosphonate dimers
QScience Connect 2012, 10 (2012); https://doi.org/10.5339/connect.2012.10
/content/journals/10.5339/connect.2012.10
/content/journals/10.5339/connect.2012.10
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  • Article Type: Research Article
Keyword(s): 28-membered bisphosphonates, cyclic phosphonates, Mitsunobu macrocyclization and Synthetic lipids

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