71979-00-5Relevant academic research and scientific papers
The use of ultrastable y zeolites in the Ferrier rearrangement of acetylated and benzylated glycals
Levecque, Pieter,Gammon, David W.,Jacobs, Pierre,De Vos, Dirk,Sels, Bert
, p. 828 - 835 (2010)
The Ferrier rearrangement of a selection of protected glycals was successfully performed using a commercially available H-USY zeolite CBV-720 as catalyst, selected after screening a range of similar catalysts. By incorporating either alcohols, thiophenol, trimethylsilyl azide or allyltrimethylsilane in the reaction it was shown that a range of O-, S-, N- and C-glycosides could be formed. With benzylated glucal and galactal in particular, use of the CBV-720 catalyst led to significantly higher yields of the 2,3-dehydroglycosides than previously reported.
13C NMR analysis of 3,6-dihydro-2 H -pyrans: Assignment of remote stereochemistry using axial shielding effects
Bartlett, Mark J.,Northcote, Peter T.,Lein, Matthias,Harvey, Joanne E.
, p. 5521 - 5532 (2014/07/08)
The rational analysis of 13C NMR axial shielding effects has enabled the assignment of remote relative stereochemistry in 3,6-oxygen-substituted 3,6-dihydro-2H-pyrans. Comparison of the 13C NMR shifts of equivalent centers in cis- an
Steric constraints against [3,3]-sigmatropic rearrangement of allylic azides. A convenient approach to β-L-4-aminopent-2-enoglyceropyranosides
Fava, Cristiana,Galeazzi, Roberta,Mobbili, Giovanna,Orena, Mario
, p. 2731 - 2741 (2007/10/03)
Starting from alkyl α-D-4-0-methanesulphonylpent-2-enoglyceropyranosides 13a-c, nucleophilic substitution carried out with polymer-supported azide ion led to regioisomeric mixtures of the azides 14a-c and 15a-c. An analogous result, due to a [3,3]-sigmatr
