Transient silylation of the guanosine O6 and amino groups facilitates N-acylation.
[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.
Fan
Yupeng
Y
Department of Chemistry and Chemical Biology, 610 Taylor Road, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, USA.
Gaffney
Barbara L
BL
Jones
Roger A
RA
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
D007202:Indicators and Reagents; D012821:Silanes; D006151:Guanosine; D010100:Oxygen