My ipod gen 2 does not sync with the latest itunes

I reset my ipod gen 2 to factory settings and version 4.2.1 will not sync with the latest iTunes.

Are you using the USB docking cable that came with that shuffle (it has a mini-dock at the shuffle end)?  The docking cable for the current 4th (and 3rd) gen shuffle fits, but it will not work.  The connector is different.
When you say, "does not sync with iTunes," do you mean it does appear in iTunes (in the sidebar under DEVICES) but does not sync, or that it does not appear in iTunes at all?

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