Improved synthesis of 1,3-disaccharides, obtained diastereomerically pure by [4+2] hetero cycloadditions between glycals and -thiono- -keto- -lactones, has been reported. The choice of appropriate protecting groups for -keto- -lactones, stable under cycloaddition conditions employed, sensibly shortened the synthesis of heterodienic precursors. The first example of a -oxy-imino- -lactone synthesized from -keto- -lactones was also reported. Molecular modeling and conformational evaluations about the cycloaddition features allowed tentatively rationalizing the experimental results. © 2009 Taylor & Francis Group.
Gabrielli G., Melani F., Bernasconi S., Lunghi C., Richichi B., Rollin P., et al. (2009). Stereoselective synthesis of 1,3-disaccharides through diels-alder reactions: Part 2[ ]: Convenient protecting groups for heterodienes and conformational evaluations. JOURNAL OF CARBOHYDRATE CHEMISTRY, 28(3), 124-141 [10.1080/07328300902752223].
Stereoselective synthesis of 1,3-disaccharides through diels-alder reactions: Part 2[ ]: Convenient protecting groups for heterodienes and conformational evaluations
Lunghi C.Membro del Collaboration Group
;
2009
Abstract
Improved synthesis of 1,3-disaccharides, obtained diastereomerically pure by [4+2] hetero cycloadditions between glycals and -thiono- -keto- -lactones, has been reported. The choice of appropriate protecting groups for -keto- -lactones, stable under cycloaddition conditions employed, sensibly shortened the synthesis of heterodienic precursors. The first example of a -oxy-imino- -lactone synthesized from -keto- -lactones was also reported. Molecular modeling and conformational evaluations about the cycloaddition features allowed tentatively rationalizing the experimental results. © 2009 Taylor & Francis Group.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
