76696-11-2Relevant 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.
SYNTHESES OF THE CHROMOMYCINONE SIDE CHAIN FROM CARBOHYDRATE PRECURSORS
Thiem, Joachim,Wessel, Hans-Peter
, p. 3571 - 3574 (2007/10/02)
Appropriate dithiane derivatives of D-threo configuration were prepared starting with D-arabinose and D-galactose, respectively.Their dianions served for nucleophilic additions to model aldehydes, thus comprising syntheses of the complex side chain of chr
