AI Article Synopsis
- The triphenylmethyl (Tr) group in 5'-O-Tr-2'-deoxynucleosides can undergo a transfer process, resulting in 3',5'-bis-O-Tr and 3'-O-Tr products, facilitated by anhydrous copper, iron, or nickel sulfates.
- If phenylmethanol is added to the reaction, detritylation occurs, leading to the formation of phenylmethyl triphenylmethyl ether.
- The behavior of the t-butyldimethylsilyl (TBDMS) group in 5'-O-TBDMS-2'-deoxynucleosides is comparable to that of the Tr group, with these types of transetherifications
Article Abstract
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.
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| http://dx.doi.org/10.1080/15257770802257846 | DOI Listing |
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