222417-80-3Relevant academic research and scientific papers
Synthesis of sugar-derived 2′- and 3′-substituted furans and their application in Diels - Alder reactions
Jarosz, Slawomir,Mach, Mateusz,Szewczyk, Katarzyna,Skora, Stanislaw,Ciunik, Zbigniew
, p. 2955 - 2964 (2007/10/03)
A convenient synthesis of 2′- and 3′-furyl sugars in which the furan and the sugar parts are directly connected is presented. The key step comprises HF-py-induced cyclization of α,β-unsaturated carbonyl compounds (ketones or aldehydes) possessing terminal hydroxymethylene groups protected as TBDPS ethers. Treatment of such furan derivatives with N-phenylmaleimide under high-pressure conditions (11 kbar) produces the corresponding [4+2] adducts, with the endo forms predominating. At p = 1 atm and T = 20 °C, however, the exo isomers are formed as the main products. The [4+2] adducts undergo retro Diels-Alder reactions at elevated temperatures at atmospheric pressure.
