A 4.060" bore and 4.00" stroke would get you 414". I would never do it though as you would need to do a lot of special stuff to get it to work - .800" small base circle cam, 2.00" or even 1.88" Honda style rod journals, short fill the block, serious grinding on the oil pan rails, etc.
Even after getting an engine like this together there would be some inherent reliability problems. Very short piston skirts would be prone to rocking in the bores and premature wear, poor rod to stroke ratio, and more . . .
It would be a ton cheaper to just buy an aftermarket 400 block, build a 400, and be done with it. Unless you were racing in some odd ball class that required a 4.00" bore I can't see any reason to ever do it.
IMO 383 or 388 would be right about the max I would ever do with a 350 block. Although you might be able to make a 3-7/8" stroker work (that would make an SBC 396) . . . 3-7/8" stroker is fairly common these days to do with a 400 block to make a 420" motor so the parts would for the most part be available (pistons might be hard).
PS. ever get that roller cam in?
E85 racer and E85 carb builder
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68 Camaro, E85 powered 427" small block. 9.96 @ 133 MPH, 1.319 sixty foot on motor. 5.92 eighth @ 116 with a 1.42 sixty breaking beams with back tire on the bottle