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Nucleic Acids Research, 1985, Vol. 13, No. 14 5215-5231
© 1985

Articles

Action of acid on oligoribonucleotide phosphotriester intermediates. Effect of released vicinal hydroxy functions

Colin B. Reese and Philip A. Skone

Department of Chemistry, King's College Strand, London WC2R 2LS, UK

Received June 12, 1985. Accepted June 21, 1985.

When 2'-O-methoxytetrahydropyranyl-5'-O-(9-phenylxanthen-9-yl) uridylyl-(3'<-5')-(2' ,3'-di-O-acetyluridine) 2-chlorophenyl ester (9) is treated with zinc bromide in dichloromethane-propan-2-ol (85:15 v/v) at room temperature, under stringently anhydrous conditions, the corresponding 5'-unblocked dinucleoside phosphate (10) is obtained in 86% isolated yield; however, when no special precautions are taken to exclude moisture, (10) is obtained in only 72% yield. The removal of the 5'-O-(9-phenylxanthen-9-yl) protecting group from (10) with a protic acid (phenyl dihydrogen phosphate) appears to be much less selective and efficient. 80% Acetic acid promoted removal of the methoxytetrahydropyranyl protecting group from the isomeric fully-protected uridylyl-(3'<-5')- and uridylyl-(2'<-5')-uridine derivatives [(11) and (21c), respectively] leads to virtually identical mixtures (Figures 1a and 1b respectively] of the partially-protected dinucleoside phosphates [(14) and (15)], 2' ,3'-di-O-acetyluridine (8), 5'-O-acetyluridine 2' ,3'-cyclic phosphate (16), and 5'-O-acetyluridine 2'(3')-phosphates [(18) and (17)].


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