Haven't seen this one before so thought I'd give it a go. This is the reformed Orochimaru with his arms restored and alive Itachi with no sickness.
Rules:
Fair fights, no plot armor.
Both of them encountered each other before.
Itachi's YM can only defend from one direction and it is strictly a shield, TB can only seal living things that the tip pierces and is strictly a sword.
Orochimaru is limited to two edos, Edo Konan and Edo Kimimaro.
Who would win and how?