backup and encrypt file by file AND only whats needed?

Hey guys,

I'm thinking about this issue for weeks now and found no solution. So I'm very very thankfull for every hint, tip or thought to get closer to a solution.

The task:
I have a lot of small and big files in one folder (circa 50GB) which I like to store encrypted on a cloud drive on a daily base. Of course I would like to upload only new and chanded files to the cloud after (long) initial upload.

Ideal situation:
I start toucan every day and it creates for every file in C: (=source) an encrypted (and optional zipped) version in F: (=targaet) if the file has changed or is new. If the file is unchanged it leaves the encrypted (and optional zipped) file as it is.
After toucan is finished I start an SFTP sync program which uploads only files with a newer date as on the cloud.

My issues:
- I can't use differntial backup for the mass of my files. Furthermore it won't deal with deleted files.
- I can't use encryption dialog cause there's no backup/sync mechanism in there.
- ...

I hope I've missed some features of toucan to solve this issue cause it's a really great program! Probably it's possible with scripting?

Thanx for your answers
Soko