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CMS Development Magento

Magento2.3 Add a custom filter as checkbox

here is a very special question ( hope you all understand the request ).

  1. i want to add in a adminhtml listing grid a custom checkbox filter.

  2. If this checkbox is checked i need to sort the full items in an other way.
    Meaning, i need to Select all entities in my custom table and do a special order direction by using a subselect ( order all items first which has one SKU ). So for this i think i have to build a native query.

  3. I need to add a custom column SKU which has only a value if the Entitiy has only one SKU.

So, my Question is:
– How can i add a custom checkbox filter
– How can i manipulate the Filter Query if this Checkbox is set against a custom native query
– How can i only fill a custom column (which are not exiting in the table) with own value

I do not find any solution of this in the Magento DEV Pages, so i hope some can tell me the LIST FILTER XML Syntax and the Classes which i have to investigate.

Thanks and happy weekend.

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