10083-80-4Relevant academic research and scientific papers
Bypassing stereoselectivity in the early steps of alkaloid biosynthesis
Bernhardt, Peter,Yerkes, Nancy,O'Connor, Sarah E.
, p. 4166 - 4168 (2009)
Total synthesis of glycosylated seco-iridoid stereoisomers allows the identification and bypassing of the stereoselectivity of early steps in monoterpene indole alkaloid biosynthesis.
1-O-vinyl glycosides via Tebbe olefination, their use as chiral auxiliaries and monomers
Yuan, Jialong,Lindner, Kristof,Frauenrath, Holger
, p. 5457 - 5467 (2007/10/03)
A series of anomerically pure 1-O-formyl glycosides 1 was prepared and converted into the corresponding 1-O-vinyl glycosides 2 by Tebbe olefination. The unsubstituted vinyl glycosides were obtained as anomerically pure compounds in good yields, and the me
Synthesis of vinyl glycosides and carbohydrate vinyl ethers from mixed acetals: A hetero-Diels-Alder approach to deoxygenated disaccharides
Hughes, Kevin D.,Nguyen, Tuan-Linh N.,Dyckman, Damian,Dulay, Doreen,Boyko, Walter J.,Giuliano, Robert M.
, p. 273 - 282 (2007/10/03)
A new method for the synthesis of vinyl glycosides and carbohydrate vinyl ethers is described. Mixed acetal glycosides and other types of carbohydrate mixed acetals are treated with TMS-triflate and an amine base, conditions developed by Gassman for the synthesis of enol ethers from acetals. The elimination proceeds regioselectively in most cases but also gives silyl ethers as side products in others. The hetero-Diels-Alder reactions of carbohydrate 3-O- and 6-O-vinyl ethers with ethyl (E)-ethoxymethylenepyruvate were carried out as part of a model study for the synthesis of deoxygenated disaccharides of antibiotics.
