Harley-Davidson recommends their 20W50 petroleum based oil for the engine. You can use the H-D Syn 3 20W50 synthetic oil in the engine but I don't recommend it in the primary/transmission area. You can use any 20W50 oil as long as the API rating has a "C" rating for use in diesel engines. Look for the round circle somewhere on the container that had the API initials in it. It should say something like "SJ/CG". What you're looking for the "C" rating. If you wish to use a specific brand of oil, got to their website and look for their recommendations.
In the transmission, Harley recommends their Semi-Synthetic Primary and Transmission lubricant for Sportsters. The lube lubricates both the primary and the transmission on the Sportster. I don't recommmend full synthetic transmission lube on any bike built before 1995 as it will cause the gears to run noisey. In 1995, Harley changed the back cut on the gears and this made use of full synthetic lube more quiet running. Of course, you can use the full synthetic from a lubrication view point. It's just a bit noisey for my taste.
Whatever you use, make sure you go online and check the manufacturer's suggestion for use.
Good Luck
Steve
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