I'm voting for Yes
Lead pipes can be hermetically sealed. It's lead. It could be hermetically sealed with a candle (well... not a candle... but if they can extrude lead pipe they can obviously melt it).
It's possible that the Romans had springs. This is good! Because the manufacturing tolerances of the pipe probably wouldn't allow even a loose-fitting canister. BUT! Throw some spring-loaded legs with wheels on the thing such that a smaller canister can roll along with shock absorption... now we're cooking with gas!
But, those springs have consequences. No vacuum. But... that could easily be fixed with a leather collar to seal around the canister. More complex than I like... but it's solving problems.
I'm not super fond of pneumatics for this purpose. I don't believe sealing the pipe is the problem. I do believe creating the vacuum in the first place could be. Pumps are good for moving fluids, but you need really, really, really well sealed pumps to create even a mediocre vacuum.
Water, on the other hand.... Fill the pipe with water from the sending end. When the canister arrives, the recipient closes a ball valve, allowing the water to drain on both sides. How does the sender know when to let the water drain? When the pressure equalizes.
Now, officially, measuring pressure wasn't something that happend until the 1500s. But it wouldn't be hard to have a small pipe affixed to the main line, probably pointing up, such that when the line pressurized a spray of water came out of it ringing a bell. That would tell the sender to turn off the water and let it drain. The line would need to be designed such that the canister didn't fall back as the water drained. Hey... you might not even need the valves I mentioned. All you need is the ability to turn water on from both sides of the pipe.
So, yes, I believe it's plausible for an alternate-history story.