Carbohydrates as future drugs. Synthesis of (2-naphthyl) β-D-xylopiranoside or XylNap and subsequent transformation of 2- and 4-positions.

Identifier:  TFG:1376

Handle: https://hdl.handle.net/20.500.11797/TFG1376

Authors:  Sendra Viscarro, Jana

Abstract:
Carbohydrate chemistry has important implications for the biochemistry of living organisms. The present work describes the development of methodology towards the selective modification of the 2- and 4-positions of xylose. First of all, (2-naphthyl) β-D-xylopyranoside (XylNap) was synthesized from xylose. In order to achieve this, glycosylation, protection and deprotection reactions have been developed. Further reaction of XylNap to selectively protect two of the three hydroxyl groups lead to a mixture of two isomers: one isomer with an unprotected hydroxyl group in the 2-position and one with the hydroxyl group in the 4-position. The selective inversion of the stereochemistry of the unprotected hydroxyl groups was attempted on the mixture of the two isomers. This resulted in a mixture of products. It was possible to observe the desired products, where inversion of the sterocentre has occurred. However there was also a significant amount of dehydration byproduct observed.