If you're using the Sony Library software, Synching should be automatic.
All you have to do is:
1. have at least 1 collection, or 1 book, in your library.
2. connect your Reader
3. in the left hand panel of the Library, click the triangle next to the Reader icon. This expands the REader contents
4. click the Sync icon in the Reader's contents
5. In the right pane, select the items you want to synch
Synch will occur automatically, or you can click the Synch Now button
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