191348-58-0Relevant academic research and scientific papers
Efficient synthesis of 5-thio-D-arabinopyranose and 5-thio-D-xylopyranose from the corresponding D-pentono-1,4-lactones
Lalot, Jerome,Stasik, Imane,Demailly, Gilles,Beaupere, Daniel
, p. 2241 - 2245 (2003)
5-Thio-D-arabinopyranose (5) and 5-thio-D-xylopyranose (10) were synthesized from the corresponding D-pentono-1,4-lactones. After regioselective bromination at C-5, transformation into 5-S-acetyl-5-thio derivatives, reduction into lactols and deprotection afforded the title compounds in 49 and 42% overall yield, respectively.
Regioselective halogenation of pentono-1,4-lactones. Efficient synthesis of 5-chloro- and 5-bromo-5-deoxy derivatives
Bouchez, Veronique,Stasik, Imane,Beaupere, Daniel,Uzan, Raoul
, p. 139 - 142 (2007/10/03)
Treatment of unprotected D-ribono, D-arabinono and D-xylono-1,4-lactones with either thionyl chloride or thionyl bromide in dimethylformamide led to 5-chloro- or 5-bromo-5-deoxy derivatives in 70%-95% yields. Under the same conditions, D-lyxono-1,4-lactone resulted in the 2-halogeno compounds.
