Recently, I was trying to use Microsoft Active Synch 4.5 to Synch my Windows Mobile with my laptop OS i.e. Windows Server 2008.
But, it seems it doesn't work that way.
Solution - Windows Server 2008 supports in built feature that is Windows Mobile Device Center 6.1. In order to make this work, you need to Add an option feature called "Desktop Experience". This you can find in Administrative Tools > Server Manager > Features > Add Feature > Check mark Desktop Experience and there you go.