82087-42-1Relevant academic research and scientific papers
Oxidative decarboxylation of mandelate ethers and α-substituted phenylacetates via dioxetanone generation
Heckmann,Alayrac,Mioskowski,Chandrasekhar,Falck
, p. 5205 - 5208 (2007/10/02)
Mandelate ethers are oxidatively decarboxylated via in situ generated dioxetanones using (t)BuOK and air at ambient temperature leading, after hydrolysis, to the benzoic acid and the corresponding alcohol. The reaction can be extended to α-substituted phenylacetates.
Chiral Building Units from Carbohydrates, VI. - Synthesis of (2R,5RS)- and (2S,5RS)-2-Ethyl-1,6-dioxaspirononane (Chalcogran) from D-Glucose
Redlich, Hartmut
, p. 708 - 716 (2007/10/02)
Starting from D-glucose the syntheses of the title compounds (15 and 25) are described.Key compounds are the tetradeoxytrimethylenedithioacetals 11 and 23 which lead by the Corey-Seebach reaction with the THP-blocked 3-bromo-1-propanol to the fully blocked, open-chained products 13 and to the (S)-analogous compound.Mild cleavage of the dithiane group and the THP-protective groups yields after spontaneous cyclisation 15 and 25.The open-chained mono-ol 11 with D-configurated hydroxyl group can be converted into the L-configurated product 22 by esterification with benzoic acid/ triphenylphosphane/ diethyl azodicarboxylate.
