because of Code Composer Studio for DSK is evaluation copy, you can not upload the files more than 256K (for program memory).
accordingly you must sale full version of CCS from TI. but it is so expensive.
the other method for upload file to the Data memory, you can use RTDX (Real time data exchange) to communicate with host PC. for this, you must develop a host software used RTDX runtime library with C++ or VB. and you can communicate the DSK used RTDX functions.
regards
tmk 8)