So, as a mild departure from "real world" framing...
I assume that your situation is a cap crunch, and you're offering variations of contracts trying to make the first year affordable. The problem is that the player much prefers money soon to money later. So, your summaries of the total contract value, even once we see the total bonus, are telling part of the story but not all of it, presumably...
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He wants $316M over 5 years, including a $47M signing bonus. So, I'm not new to this business, thus we offered him $318M over 5 years, including a $85M bonus.
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That sounds like it ought to work, but... all i can suggest is more bonus. The default request is usually pretty backloaded in base salary anyway, so presumably you're backloading it even more...not sure what to suggest but if you have the capacity now, adding bonus is way more effective than adding more base salary in, say, year three.
I think you likely know all this and I'm not helping...but just in case, that's likely the path if you can squeeze it short term.