76696-05-4Relevant academic research and scientific papers
Studies on D-Threose Derivatives and on the Preparation of the Olivin Side Chain
Thiem, Joachim,Wessel, Hans-Peter
, p. 2216 - 2227 (2007/10/02)
Oxidative cleavage of the D-arabinitol derivative 3 yields the dimer 5 of benzylidene D-threose.In pyridine solution D-threose (11), obtained by acid hydrolysis, predominatly represents a mixture of the anomeric furanoses 7 and 12.By either kinetic or thermodynamic isopropylidenation of the trimethylene dithioacetal 9 preparation of the terminal or the non-terminal dioxolane 14 or 16, respectively, is achieved selectively.Starting with 16 several steps lead to the crystalline 4-deoxy-D-threose trimethylene dithioacetal (25), by metallation of which the formation of a trianion could not be demonstrated.However, both the diastereomeric model compounds 28 and 30 of the olivin side chain were prepared via dimetallation of 14.
