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It's towards the very end, but you don't have to side with them. You do have to give them a network scanner that you used, which will open up a quest that leads you to becoming a Paladin. I don't want to say more otherwise it may spoil some of the story for you.
Yeah, its the second highest rank in the entire Brother Hood of Steel faction, right behind elder. You can only become a sentinel by beating the game with the Brother Hood of Steel.
http://fallout.wikia.com/wiki/Elder_%28rank%29?file=Bos_rank_sentinel_icon.png#Elder
Also bos ending should set player as Elder,but guess bethasada ran out of time to make bos questline longer.
Unless of course, the DLC features strictly companion quests that allows you to 'ice' the wannabe hitler. One can hope now, can they?