131530-71-7Relevant academic research and scientific papers
Aminocyclopentanols as sugar mimics. Synthesis from unsaturated bicyclic lactones by Overman rearrangement
Bojstrup, Marie,Fanefjord, Mette,Lundt, Inge
, p. 3164 - 3171 (2007)
Bicyclic cyclopentane lactones, prepared from bromodeoxyaldonolactones, were transformed into aminocyclopentanols with an Overman rearrangement as the key step. Two of the compounds prepared, 7 and 19, were found to be good inhibitors of jack bean α-mannosidase and β-d-N- acetylglucosaminidase, respectively. The Royal Society of Chemistry.
THE FOUR-CARBON ELONGATION OF THREE-CARBON CHIRAL SYNTHONS USING 2-(TRIMETHYLSILOXY)FURAN: HIGHLY STEREOCONTROLLED ENTRY TO ENANTIOMERICALLY PURE SEVEN-CARBON α,β-UNSATURATED 2,3-DIDEOXYALDONOLACTONES
Casiraghi, Giovanni,Colombo, Lino,Rassu, Gloria,Spanu, Pietro,Fava, Giovanna Gasparri,Belicchi, Maria Ferrari
, p. 5807 - 5824 (2007/10/02)
The BF3-promoted addition of 2-(trimethylsiloxy)furan to three carbon synthons derived from D- and L-glyceraldehyde, D- and L-serinal, and imines thereof furnishes C7 α,β-unsaturated 2,3-dideoxy-aldonolactone derivatives in high yield, with very high level of diastereoselection.In all the cases, compounds having 4,5-threo:5,6-erythro relative stereodisposition preferentially emerge from the reactions, accompanied by only marginal amounts of 4,5-erythro:5,6-threo epimers.An empirical rule for the rapid assignment of the configuration at C-4 (γ-carbon) of γ-substituted unsaturated and saturated β-butyrolactones is given, based upon the sign of the optical rotation values.
