Hey,
Try running a disk check on the iPod using the tools provided by Windows.
1. Plug in your iPod and close iTunes.
2. Go to "My Computer". Click on the iPod drive once. Go to File, and then click Properties.
3. Go to the Tools tab. Under "Error Checking", click Check Now.
4. Check both boxes. One says "Automatically fix file system errors" and the other says "Scan for and attempt recovery of bad sectors". Place a check mark next to each of these options and hit Start.
The scan may take several minutes or more to complete, but once it has, go ahead and restart iTunes, and try re-syncing files to your iPod.
Others have had luck with the solution provided in this Apple support document. It does say error 50 but may apply to your situation as well. It's worth a shot.
http://support.apple.com/kb/TS1539Hope this helps :-)