I had a '79 300sd, those U-shaped hoses are a bear when the material ages and gets stiff and deformed (sort of like me).

You said gasketS. You don't really need one at the air cleaner end, as I remember (I certainly never had one).

Boil up some water in a pan (or on a hot day, try leaving it in direct sun for a few hours). Either way, try to make the end that goes over the turbo inlet it more pliable.

Remove the round seal that isn't cooperating and put it aside, then work the end of the now-hopefully-pliable hose around the turbo inlet, to try to temporarily expand it a bit.

It's a huge PITA job but it can be done....

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Mac
2002 e320 4matic estate│1985 300d│1980 300td
Previous: 1979 & 1982 & 1983 300sd │ 1982 240d

“Let's take a drive into the middle of nowhere with a packet of Marlboro lights and talk about our lives.” ― Joseph Heller, Catch-22