HT203356: If iTunes doesn't respond when you connect an iOS device
Learn about If iTunes doesn't respond when you connect an iOS device
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Oct 16, 2012 11:50 AM in response to mmm2007by turingtest2,iPod Classic went on the fritz today just after syncing. Couldn't restore via iTunes, kept getting 1439 errors, Windows wouldn't format as FAT32, claimed the "Volume is too big for FAT32". Finally tracked down EaseUS Partition Master Home Edition (Free) and formatted as FAT32 with 128k clusters. The iPod is filling back up again. Might be worth a shot here...
See also this post on iPod classic troubleshooting.
tt2