Hmm.
I suppose I should check in more often...
I expect you've already arrived at a specific transverse VW 5 speed 'box setup already, but..
FWIW, VW has been using nothing but 6, and 7-speed transaxles in anything but the most pathetically cheap (like 2.slow) applications, since 2003 or so.
Our (gasoline turbo-powered) GP/S Passat uses a stone-stock longitudinal FWD 6-speed found in USA-market '05-'08 2WD Audi A4s. Model: 01X. Code: GVD.
3.75 R&P, .658 6th. So with an effective top ratio of 2.4675 and 23"-26" tall front tires, we've made a zillion 200+mph Bonneville runs. We allow it to spin to 9000 rpm, though, so your Diesel, -even raggedly spun to 6500- will likely run out of gear, with only 350 or so HP, if your drag area is remotely like the Passat. The Euro TDI version of the 01X has a .575 6th, giving it a better (2.15625) chance of high speeds with a diesel.
All that said... None of that really matters, since you are not cutting your pickup apart any time soon and twisting the engine 90 degrees.
But my point is that -while spending $10,000-$20,000US on a dreamy custom gearbox totally sounds really fun. your wife and kids will not like life on the street, even in Herky-Jerky MO!
There are plenty of transverse 6-speed combinations.
Example:
USA 2009 Jetta TDI 2.76 r&p, .81 6th= 2.2356 overall
2010-2013 Jetta TDI 2.76 r&p, .72 6th= 1.9872 overall
The 6 speeds actually have less overall length than the 02A/02J 5 speeds, and have room for a Very Large flywheel and clutch. And until you start making over 600-700 ft.lb, you won't break one. Let me know if I can help.