Hi Everyone,
Can somebody help me? First, I need to protect one of OH group of 1,10 decandiol ( I have the plan to use TBDMScl / imidazol,DMF, rt) .Then I need to react it with my compound. At the end, sine I have an ester and carbonate group, if I use TBAF to deprotect the OH group, does not it affect my both ester and carbonate group? Thanks in advance!
TBAF contains usually three water molecules per molecule of the reagent, and this means that hydroxide-anion can be generated. This is usually a small amount that is insignificant for other adverse reactions.
But if you set a goal to achieve quantitative yields, you should turn to truly anhydrous reagents, such as HF complexes with triethylamine or pyridine. According to our data, the complexes with pyridine are so mild that allow to remove quantitatively TBDMS-protection of oligonucleotides.
Andrei Rogoza Thank you so much for your helpful comment. And can you please tell me what exactly HF complexes are ? Is there any special ?Based on protecting group book by Green, it says aqueous HF,CH3CN (5:95). Do you mean for example a complex like this or can I ask you if you can provide me with your procedure if you do not mind please? Appreciate it!
Check links below
https://www.sigmaaldrich.com/RU/en/product/aldrich/184225
https://www.sigmaaldrich.com/RU/en/product/mm/814371
Please keep in mind that HF reagents are corrosive for glass, so plastic is preferable for reaction. NaHCO3 or CaCl2 hydrate or silicagel are suitable to neutralize fluoride during wet (aqueous) work-up
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