K. Lesiak, Kyoichi A. Watanabe, Jay George
Feb 20, 1998
Citations
0
Influential Citations
13
Citations
Journal
Journal of Organic Chemistry
Abstract
2-(4-Nitrophenyl)ethyl methylenebis(phosphonate) (6) was prepared by reaction of equimolar amounts of 2-(4-nitrophenyl)ethyl alcohol and methylenebis(phosphonyl) tetrachloride in the presence of tetrazole. Compound 6 was further converted into the corresponding 4-nitrophenylethyl trisanhydride intermediate 7 by dehydration with diisopropylcarbodiimide (DIC). Reaction of 7 with either 2‘,3‘-O-isopropylideneadenosine (8a) or 2‘,3‘-O-isopropylideneguanosine (8b) afforded, after hydrolysis, the desired P1-[2-(4-nitrophenyl)ethyl]-P2-(2‘,3‘-O-isopropylideneadenosin-5‘-yl) methylenebis(phosphonate) (9a) and guanosine analogue 9b, respectively. A similar treatment of intermediate 7 with 3‘-O-acetylthymidine (12a), 3‘-O-acetyl-2‘-deoxy-N4-benzoylcytidine (12b), 3‘-O-acetyl-2‘-deoxy-N6-benzoyladenosine (12c), and 3‘-O-acetyl-2‘-deoxy-N2-isobutyrylguanosine (12d) gave the corresponding 2-(4-nitrophenyl)ethyl methylenebis(phosphonate)s 13a−d. These compounds as well as 9a,b were treated with 1,8-diazabicyclo[5.4.0]u...