Friday, July 2, 2010

now that's GLOBAL deprotection

I stay the hell away from sugar chemistry. In fact as a general rule I try to not even read papers about it. It's not that I don't like it, it's that it scares the shit out of me.

Sugar chemistry is an odd field where it seems that chemistry from other common areas doesn't work, and chemistry that works in sugar chemistry doesn't always translate to general organic reactions well. The reactions within the field, unfortunately, don't always work either.

When I happened on this today, I would have otherwise skipped it except for the compelling graphical abstract, that I have blown up here:

JOC ASAP

These guys took off 21 TBS protecting groups all at once. I gather from the text this may not be all that unusual, but it sure surprised me, especially when it is presented in visual form. The overall yield was ~28% which is an average of ~94% per protecting group. I have, unfortunately, had a lot of worse yields in taking a single protecting group off of a robust molecule in the past.

Sure puts a total synthesis "global deprotection" in a different light for me. Kudos to the sugar chemists, you insane fuckers.

4 comments:

Mike said...

i never want to see another sugar again after i graduate.

scientist 1 said...

Here, here!

John said...

Going from 6 g to 300 mg in one step is always good for morale

scientist 1 said...

Maybe you should do the transformation protecting group free, just to show those pussies how it's done.