Never tried anything like this big. But... you could sync 50 gensets if each has a syncroniser, and there is a bus to connect them too that has a stable reference frequency. So 50 gensets, each with its own syncroniser, onto the utility should be OK, they'll come on in sync. And syncing to the utility is realtivey easy, as its big and the genset typically isn't. If you connect a genset to the utility and the phase is wrong, the genset will cme into sync, if the breakers hold. The genset may be literally thown halfway across town in the process, though.
50 gensets cold-start is harder, as there isn't a stable reference, and not a big daddy reference either. You would need one to take the bus, and be stable, and then the rest could follow.
This relies on the syncronisers being perfect, of course, as modern electronic syncronisers are. The electro-mechanical syncronisers from my youth wouldn't work in this scenario, as they were not accurate, and so there was a pulling or pushing as the genset came online. With 50 of those in quick sucession I suspect it would end quite badly.