title: Transient silylation of the guanosine O6 and amino groups facilitates N-acylation.
abstract: [reaction: see text] The formation of a guanosine derivative silylated at both the O6 and amino groups was identified by (15)N NMR. This intermediate allows facile reaction with acetyl chloride or phenoxyacetyl chloride to give in high yield the corresponding N-protected guanosine derivatives, suitable for use in RNA synthesis. The acetyl and phenoxyacetyl amino protecting groups are, respectively, 4 and 230 times more labile than the isobutyryl group to methylamine/ethanol deprotection.
authors.affiliation: Department of Chemistry and Chemical Biology, 610 Taylor Road, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, USA.
authors.forename: Yupeng
authors.initials: Y
authors.lastname: Fan
authors.forename: Barbara L
authors.initials: BL
authors.lastname: Gaffney
authors.forename: Roger A
authors.initials: RA
authors.lastname: Jones
mesh_terms: D049148:Aminoacylation; D006151:Guanosine / Q000031:analogs & derivatives* / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry; D012821:Silanes / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D007202:Indicators and Reagents; D012821:Silanes; D006151:Guanosine; D010100:Oxygen