Optimization of Reactions Opening Cyclic Ring of Pentose Sugar Derivatives through Dithioacetalisation Reactions

Abstract

Ring-opening reaction of cyclic pentose sugar derivatives of 2,3,4-Tri-O-benzyl- D-xylopyranose
to derivatives of acyclic 2,3,4-Tri-O-benzyl-D-xylose-Dipropyl dithioacetal been done and
optimized. The reaction was performed using a precursor propanathiol with concentrated HCl.
Optimization of reaction conditions was conducted by varying propanathiol concentration,
reaction time and optimization of the reaction temperature which the product ioslation conducted
using a variety of solvents. The results of this reaction was obtained 2,3,4-Tri-O-benzyl- Dxylose-
Dipropyl dithioacetal with the highest randemen (97%), better than the previous reaction
through propanathiol excessive concentration, reaction time of 2 hours and the temperature of the
reaction at room temperature. Product Isolations using solvent dikloromathane more effective
than the use of other organic solvents. Purification of reaction products is done through a column
chromatography using a solvent mixture of 20% ethyl acetate-hexane.

Keywords: Optimization, Cyclic Ring, Dithioasetalisasi