do you need a programmer and can you only program it once? Do I have to learn a whole new language/library to use it?
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Yes, you need a programmer. Actually, it's apparently designed to use a programming adapter in conjunction with a conventional EPROM programmer (for some obscure 12V Toshiba EPROM...)
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Each chip can only be programmed once. The idea is that this is better for development than the usual ROM-based 4-bit cpus. I couldn't find anything that claimed to be a simulator...
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Toshiba apparently has (had) an assembler and a C-like-language compiler for this, for DOS (or DOS window in windows.) But that was a product of indeterminate price, I don't know any details, and more recently all traces of this CPU have pretty much disappeared from Toshiba's site. I did find a free 3rd party assembler...