I can give you a little more information while I run a test on 64 bit java with -Xmx2500m.
We recently added 4 languages which made the total size of the artifacts increase from about 15Gb to about 20Gb. Before this increase, I have never encountered this issue.
I also have been trying to keep Jenkins up-to-date so I update regularly. That means that almost certainly, when we successfully built 15Gb of artifacts, we also ran an older version of jenkins. Also, at the time, the jenkins slave ran with the default heap size, a measily -Xmx250m. This suggests that this OOM issue may be a newly introduced.
Looking at the memory usage of java.exe on the slave, I see that it increases stepwise as it grabs another artifact to upload. At the moment, one third of the way through, it is up to 800mb peak usage.
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