536739-80-7Relevant academic research and scientific papers
RCM-based synthesis of a variety of β-C-glycosides and their in vitro anti-solid tumor activity
Postema, Maarten H. D.,Piper, Jared L.,Betts, Russell L.,Valeriote, Frederick A.,Pietraszkewicz, Halina
, p. 829 - 836 (2007/10/03)
(Chemical Equation Presented) The synthesis of a number of biologically relevant C-glycosides has been carried out through the use of an esterification-ring-closing metathesis (RCM) strategy. The required acid precursors were readily prepared via a number of standard chemical transformations followed by dehydrative coupling of these acids with several olefin alcohols 1 to yield the precursor esters 3 in excellent yield. Methylenation of the esters 3 was followed by RCM and in situ hydroboration-oxidation of the formed glycals to furnish the protected β-C-glycosides 6 in good overall yield. Several examples were converted to the corresponding C-glycoglycerolipids 17 and subsequently screened against solid-tumor cell lines for in vitro differential cytotoxicity.
Synthesis of some biologically relevant β-C-glycoconjugates
Postema, Maarten H. D.,Piper, Jared L.
, p. 1721 - 1723 (2007/10/03)
(Matrix presented) An esterification-RCM approach to a variety of biologically relevant β-C-glycoconjugates is reported herein. A range of carboxylic acids were coupled with several different olefin alcohols 1 to provide esters 3. The esters were then con
