6968-62-3Relevant academic research and scientific papers
Synthesis of carba sugars from aldonolactones. Part IV. Stereospecific synthesis of carbaheptopyranoses by radical-induced carbocyclisation of 2,3-unsaturated octonolactones
Wagner, Sussi Holstein,Lundt, Inge
, p. 780 - 788 (2007/10/03)
Three new carbaheptopyranoses, 6-deoxy-5a-carba-β-L-gulo- (8), 5a-carba-D-glycero-β-D-ido- (22) and 5a-carba-Lglycero-α-L-galacto-heptopyranose (25), have been prepared from 8-bromo-8-deoxy-2,3-unsaturated octono-1,4-lactones with L-galacto-, D-gluco- and D-manno-configuration, respectively. The key step was a regio- and stereoselective 6-exo-trig radical-induced carbocyclisation of the unsaturated octonolactones to give bicyclic cyclohexane-lactone derivatives. Reduction of the lactone moiety using Ca(BH4)2 gave the said carbaheptopyranoses. The 8-bromo-8-deoxy-2,3-unsaturated octonolactones were prepared from the inexpensive, commercially available D-glycero-D-gulo-heptonolactone and L-tartaric acid.
Acetonides of octonolactones
Bell, Andrew A.,Nash, Robert J.,Fleet, George W. J.
, p. 595 - 606 (2007/10/03)
Acetonides of the eight carbon sugar lactones, D-erythro-L-talooctono-1,4-lactone and D-erythro-L-galactooctono-1,4-lactone, readily derivated from glucoheptonolactone, are easily accessible intermediates for the synthesis of sugar mimics with six adjuvant stereogenic centres and eight contiguous carbon atoms bearing functional groups.
