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If you mean knowing if the version of a book in Calibre's library has been updatged since it was last sent to the reading device, then the answer is no.
I tend to use the Book Sync GUI plugin, and when I update a book in the library I then add it to the Sync queue to be sent to the reader when I next plug it in. That should cause the book to be resent to reader overwriting the copy already there.
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