Editing is key as well as being able to open the glass. I have done a similar shot by marking a path to follow on the ground, I shoot up until I am just about touching the glass and stop, I then open the window or door, back up, follow my path and begin recording once again and push the camera through the opening, once again stopping. Then, go outside the glass if possible, and line up with my marked path and continue out some more. Once in editing I find the proper frames to splice it together. The hardest part is staying on path which is why I like to use painters tape placed on the ground to help me. I have found that placing a small dissolve one that lasts less than a second when the camera “passes through the glass” helps add to the effect.