1025799-36-3Relevant academic research and scientific papers
2-(4-Nitrophenyl)ethyl Methylenebis(phosphonate): A Versatile Reagent for the Synthesis of Nucleoside 5′-Methylenebis(phosphonate)s
Lesiak, Krystyna,Watanabe, Kyoichi A.,George, Jay,Pankiewicz, Krzysztof W.
, p. 1906 - 1909 (2007/10/03)
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 P 1-[2-(4-nitrophenyl)ethyl]-F2-(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]undec-7-ene (DBU) which caused elimination of the 2-(4-nitrophenyl)ethyl group. The base labile 3′-O-acetyl, N4-acetyl, N6-benzoyl, and N2-isobutyryl groups of 12a-d were also removed during the DBU treatment. Thus, the 5′methylenebis(phosphonate)s of 2′,3′-O-isopropylideneadenosine (10a), 2′,3′-O-isopropylideneguanosine (10b), thymidine (14a), 2′-deoxycytidine (14b), 2′-deoxyadenosine (14c), and 2′deoxyguanosine (14d) were prepared in good yield. De-O-isopropylidenation of 10a and 10b afforded adenosine 5′-methylenebis(phosphonate) (11a) and guanosine 5′-methylenebis(phosphonate) (11b), respectively.
Synthesis of 2'-deoxynucleoside 5'-methylenebis-(phosphonate)s using 2- (4-nitrophenyl)ethyl mthylene-bis(phosphonate) as the phosphonylating agent
Lesiak, Krystyna,Watanabe, Kyoichi A.,Pankiewicz, Krzysztof W.
, p. 1857 - 1860 (2007/10/03)
2-(4-Nitrophenylethyl) methylenebis(phosphonate) (1) has been prepared by reaction of 2-(4-nitrophenyl)ethyl alcohol with methylenebis(phosphonyl) tetrachloride. Compound 1 was treated with diisopropylcarbodiimide (DIC) to give bicyclic intermediate 2, wh
