When I sync my ipod classic with iTunes it deletes all the music on my ipod

Hi everyone, I have an ipod classic 160GB and when I try to sync it with iTunes to put things like TV shows ect it deletes all the music off of my iPod (which is over 400 songs) so I have to put it all back on using another program and then when I try to use iTunes again it deletes everything. Sometimes when I put podcasts on it just deletes the music but not the podcasts, or it'll decide to the opposite. Recently it deleted all of my music and videos and just left the podcasts.
Your help is greatly appreciated,
thank you

Hello qz0rz213,
It would seem that iTunes has encountered or developed an issue in the process of trying to sync photos to your device. The best place to start would be removing the iPod Photo Cache (thus allowing for a new version to be created).
Note: Deleting this folder will not remove the original images from your library.
iTunes: Understanding the iPod Photo Cache folder
http://support.apple.com/kb/TS1314
If the issue is not resolved by removing the iPod Photo Cache, the following article goes into further steps that can both help you determine the source of this trouble and eliminate it.
Symptoms
In certain situations, iTunes may display an alert or may be unable to sync photos to an iPod or iOS device. Examples include:
After updating iOS, iTunes displays an alert that there is not enough room to sync photos
This error appears: "The iPhone/iPod touch '[device name]' cannot be synced. The required file cannot be found."
This article outlines steps to resolve these issues.
iTunes: Unable to sync photos
http://support.apple.com/kb/TS3697
Cheers,
Allen

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