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How to merge two datasets based on different time interval conditions?

I have two different datasets and would like to join Dataset2 to Dataset1.
In Dataset1, there are different CBs in each day, and there are IV 1 to 3 in each CB.
In Dataset2, there are different time intervals, for example every 1 hour, 15 min, or 5 minute.
I am looking to add conditions in left_join or fuzzy_left_join or any other way to join these two datasets as below,