It would take a near complete wiping of your farm system. Seeing as they dont do discounts for dealing for multiple players, let's see the prices you'd be looking at for each...
Choo would probably be the cheapest because he's got 1 yr left on his deal. But he is also the most explosive offensively. He was a .300/.400/.500 player from 08-10. His 2011 season is pretty much a mulligan and he bounced back well in 2012 with a very high OBP. He's likely to require at least 3 prospects, one of which would be considered a right now kind of guy (Brentz) and 2 more guys with down the line potential (Cecchini and Jacobs).
Asdrubal Cabrera has his flaws, but he is still one of the most valuable SS's in the AL and he's signed reasonably for 2 yrs. He will likely require one of the B's, preferably Bogaerts on their end to replace their big offensive producer in the middle of the diamond. You'd probably be looking at Bogaerts and a guy like Workman to make this happen.
Masterson is a guy they have zero reason to deal. He's a kid who has put together back to back 200IP seasons and had an ace level season in 2011. The funny thing is, his peripherals in the first half of 2012 were better than his season in 2011, then he fell off the wagon. Seeing as he is under control for 2 more yrs and just a year ago he was coming off an ace season, they would need to be paid at ace level to deal him. I am not saying he is an ace, just that in order for them to deal before they see what they have in 2013, they'd need an ace haul. You'd need to see Barnes, Owens, and Swihart for him, a deal the sox shouldnt and wouldnt do. Should Masterson pitch to his 2012 season, he'd be worth a ton less after 2013.
So, to get those three, you are looking at Barnes, Bogaerts, Brentz, Ceccini, Workman, Jacobs, Owens, and Swihart