You need to add a meta box and populate it with the post attachments. It is very similar to the front end code you would use, except you need to save the data.
On admin init:
add_meta_box( $id, $title, $callback, $page, $context, $priority, $callback_args ); ?>
function custom_type_metabox($post) {
$custom_box = get_post_meta();
//get all the attachments for the post and throw them in an array.
?>
//populate a checkbox list with the attachments from your array
<input type="radio" name="custom_attach" value="any" <?php if ($somestring == 'attachment') echo "checked=1";?>>
// then you need to save the data and pass it to the post using "save_post"
add_action('save_post', array('your_data'));
// add your function to verify and save data properly
This is just a simple non working example I wrote off the cuff because what your asking for is basically the same as writing a plugin, maybe this will lead you into the codex.