Dear all,
for a synthesis, we need 4'-OH-Monosaccharides (all other hydroxyl-groups should be protected, acetylated or benzylated or else...) - I am desperately looking for a working protocol to prepare these regioselective deprotected sugars ...
All strategies I tested so far are not working or have very low yields.
Does anyone have an idea, can share experience or point me to appropriate literature?
Thanks al lot in advance,
Peter
This protocol uses Sodium cyanoborohydride (sodium cyano borane) which is considerably toxic... :/ Are there alternatives?
Dear Peter, your biggest problem is that with monoS. one size does not fit all.
What sugars are you looking at? for ex. on Galactose, an easy one you can start from the OMe glycoside and then at low temp. benzoylate 2, 3 and 6. that is one example.
Do you have access to Sc Finder or Reaxis?
you can go through this paper.......
http://www.nature.com/nature/journal/v446/n7138/full/nature05730.html
I did a lot synthesis in the past related to monosaccharides, and I know that it is tough sometimes. Regarding literature, I suggested you to look at the book which I use a lot: Philip J. Kocienski, Protecting groups, 3rd Ed., Thieme.
Hopefully, this will help you.
All the best.
You can use benzylidene-4,6-O-acetals! It can be opened regioselectively (Carbohydr Res. 2011 Sep 6;346(12):1358-70)
It will depend on the targeted monosaccharide: Glc or Gal Or Man... please clarify...
1 st carry out bezylidine protection then opened with BH3THF in presencs of Bu2BOTf.
The molecule to be protected is 1-methoxy-2-deoxy-Glucose - I need the 4'-alcohol.
I understand that 2-deoxy-sugars have properties deviating from natural monosaccharides, so will benzylidene-protection work out in this case?
I already tried, but I get a tonload of side products...
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