I\'d like to send the text content of a file over the serial port, over PuTTY. I know that extensions exists such as Xmodem and Zmodem, but they all use some checksum proto
Use Plink (a command-line connection tool from PuTTY suite). It's a console application intended to automate connection tasks, like yours. Being a console application, you can redirect its input from a text file:
plink.exe -serial -sercfg ... < input.txt
See Using the command-line connection tool Plink
See also related How to execute remote command using PuTTY over Telnet.