Hello,
I don’t think that a natural sync can be made from the windows media player program.
As I too stumbled into this issue, after previously synced my sansa player directly from WMP, I have developed a python script to workaround this issue:
https://github.com/eyalitki/Playlists-Scripts
The script will export your original playlist, and convert it to a supported .m3u playlist on the music player.
Hope it will be helpful.
