There is no way.
Unless white zetsu can use Mokuton. Which I have not seen, but I am very forgetful.
Elaborate, Orochimaru can relatively counter everything in Itachi's arsenal.
I don't even see Oro beating Kakashi let alone Itachi
Kakashi > Itachi.
Needs feats to suffice. I see him obtaining Ryuu-Sennin Modo down the line anyways, on top of ridiculous reserves courtesy of Hashirama's cells, Mokuton AND all his forbidden jutsu, amplified by Senjutsu, he'll be a formidable source.
Mind you, Itachi is analytically smarter than Itachi, albeit Orochimaru has the second most knowledge in all of the manga. But, with Amaterasu hitting Orochimaru, Orochimaru will be forced to use Oral Rebirth. As the new body comes out, Itachi can manipulate the flames to go to the new body. And if things get really tricky, he can always Totsuka blitz.
But if white Zetsu can use Mokuton [scans please] Orochimaru has better chances.
Improved Shadow Clone shits on Amaterasu.
2 separate sensory abilities followed by Hiding Like a Mole, Mayfly or Attack Prevention shit on Amaterasu.
Itachi > Kakashi > Tobirama