I don't know of any shopping cart software that would do this for you. It kind of breaches that unspoken line of what software should do for you, and what you should tell it to do.
Most carts (like Magento) have the ability to set up relationships between products in which during checkout you'll automatically shown some products as either (a) what others bought or (b) what you might be interested in based on what's in your shopping cart.