Protecting groups transfer: unusual method of removal of tr and tbdms groups by transetherification.
The triphenylmethyl (Tr) group undergoes a transfer (transetherification or disproportionation) between the molecules of 5'-O-Tr-2'-deoxynucleosides in a process mediated by anhydrous sulfates of Cu(+2), Fe(+2), or Ni(+2) to yield mixtures of 3',5'-bis-O-Tr and 3'-O-Tr products. If phenylmethanol is present in a reaction medium, detritylation results with concomitant formation of phenylmethyl triphenylmethyl ether. The behavior of t-butyldimethylsilyl (TBDMS) group in 5'-O-TBDMS-2'-deoxynucleosides is exactly the same. Such type of transetherifications was not observed before for the O-Tr and O-TBDMS groups.
Cabral
Nadia L D
NL
Department of Pharmacy, UFPE, Recife, Brazil.
Thiessen
Luciano Hoeltgebaum
LH
Doboszewski
Bogdan
B
D002133:Calcium Sulfate / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods*; D015394:Molecular Structure; D009705:Nucleosides / Q000737:chemistry*; D012833:Siloxanes / Q000737:chemistry*; D013343:Styrenes / Q000737:chemistry*; D014320:Triphenylmethyl Compounds / Q000737:chemistry*
C506477:4-(tert-butyldimethylsiloxy)styrene; D009705:Nucleosides; D012833:Siloxanes; D013343:Styrenes; D014320:Triphenylmethyl Compounds; D002133:Calcium Sulfate