Borane-amine complexes--versatile reagents in the chemistry of nucleic acids and their analogs.
A new method for synthesis of N-alkylated nucleosides was developed. Exceptionally mild and selective conversion of N-acyl to the corresponding N-alkyl nucleosides was achieved by reduction with borane-amine complexes. The borane-amine complexes were also used as efficient scavengers of a 4,4'-dimethoxytrityl (DMT) cation. Neutralization of the cation eliminated the boranophosphate group degradation during acidic DMT deprotection and allowed milder acidic conditions for the deprotection.
Sergueeva
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Department of Chemistry, Duke University, Durham, North Carolina 27708-0346, USA.
Sergueev
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Shaw
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D000478:Alkylation; D000588:Amines / Q000737:chemistry*; D001880:Boranes / Q000737:chemistry*; D009705:Nucleosides / Q000138:chemical synthesis*; D019163:Reducing Agents / Q000737:chemistry; D014320:Triphenylmethyl Compounds / Q000737:chemistry
D000588:Amines; D001880:Boranes; D009705:Nucleosides; D019163:Reducing Agents; D014320:Triphenylmethyl Compounds; C060949:4,4'-dimethoxytrityl cation