I don't know much about the civvy side, but the 1.5 ton G506 4 speed will bolt up to a 50's 235 bellhousing. If the G506 4 speed will bolt up, the 5 speed G508 CCKW tranny will bolt up, but 'fitting' is another matter. I'll post some side by sides of both for reference.

A TON of people talk about putting the CCKW 5 speed in a lot of 40's 50's trucks to get that overdrive... but I've never heard of it actually working or even being done. It's possible, but the 5 speed is a monster.