193553-76-3Relevant academic research and scientific papers
Stability of regioisomeric sugar allyltins. Cleavage of the carbon-oxygen bond under radical conditions
Jarosz, Slawomir,Szewczyk, Katarzyna
, p. 3021 - 3024 (2001)
Secondary sugar allyltin derivatives [Sug-CH(SnBu3)-CH=CH2] decompose at high temperature (140°C) with elimination of the tin moiety and opening of the sugar ring. The cis-dienoaldehydes thus formed react with Ph3P=CH-CO2Me to afford the corresponding trienes, which spontaneously undergo stereoselective intramolecular [4+2] cycloaddition to optically pure, highly oxygenated bicyclo[4.3.0]nonene derivatives. Primary sugar allyltins [Sug-CH=CHCH2-SnBu3] are thermally stable and do not decompose up to 170°C.
From sugar allyltins to chiral cyclopentadienes: Radical cyclization of highly oxygenated sugar-derived dienoaldehydes
Mach,Jarosz
, p. 936 - 940 (2007/10/03)
Radical cyclization of unsaturated aldehyde: 2,3,4-tri-O-benzyl-5,6,7,8-tetradeoxy-5(E),6-dieno-oct-D-xylose (2) afforded 1(R)-hydroxy-2(S),3(S),4(R)-tri-O-benzyloxy-5(R)-[prop-1(E)-enyl]-cyclopentane (5); similar reaction of xanthate 7 derived from 2 led to 2(S),3(R),4(R)-tri-O-benzyloxy-5(R)-methyl-cyclopentane (8). The cyclization of other sugar-derived unsaturated aldehydes and xanthates was also studied.
