Stop item spawning on level reload if it has been collected AND player has passed checkpoint

So I need any items a player has collected to respawn on death, until they pass a checkpoint. After that point, anything the player has collected before there death needs to destroy itself. Been up for about 16 hours and don't have the brain function to figure out if this is something difficult or if I'm just being dumb.

Below is my checkpoint code.

 void Start()
 {
     thePlayer = GameObject.FindGameObjectWithTag("Player");
     hudController = thePlayer.GetComponent<hudController>();
     gameMaster = GameObject.FindGameObjectWithTag("GM").GetComponent<GameMaster>();
 }

 private void OnTriggerEnter(Collider other)
 {
     if (other.tag == "Player")
     {   gameMaster.lastCheckpoint = transform.position;
         PlayerPrefs.SetInt("Lives", hudController.playerLives);
         PlayerPrefs.SetInt("Beer", hudController.beerCount);
         PlayerPrefs.SetInt("Score", hudController.playerScore);
     }
 }

     

}