Two observations (with $k$ a field of char.characteristic zero):
If $A$ is a domain over a field $k$, then elements of $D(A)$ extend to elements of $D(A_S)$ for all mult.closedmultiplicatively closed sets $S$.
Your questions become easier if you ask instead about the algebrasubalgebra $\Delta(A)$ of $D(A)$ generated by $A$ and derivations: then the answer is yes to your two questions. IfNow, if $A$ is finitely generated and regular, then $D(A)=\Delta(A)$, so in this case the answer is yes for $D(A)$ too.
You'll find this in the last chapter of McConnell and Robson's book on noetherian rings.
(Finally, $D^{\leq n}(A)$ is an $A$-bimodule which is not symmetric, so tensoring with $A_f$ on one side or the other is not the same thing)