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use of the SEM protecting group in carbohydrate chemistry


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https://doi.org/10.1002/chem.201101163

I am working on synthetic routes to a glucoside.  The beta-trimethylsilylethoxymethyl (SEM) group has some attractive features (particularly in regards to deprotection), but I have only found one paper in which four SEM groups were used to protect the oxygen atoms at carbons 2-4 and 6 of a glycoside conjugated with a steroid.  They did not deprotect to the best of my knowledge, but I assume that one would use a standard recipe.  I did find a paper in which a glycoside was protected with several different groups, including one SEM.  Are there disadvantages to using the SEM group as the protecting group?  Are there reasons why it has been used more in carbohydrate chemistry?  Should I be favoring other protecting groups instead?

Edited by BabcockHall
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