TY - JOUR
T1 - Synthesis of 2'-deoxynucleoside 5'-methylenebis-(phosphonate)s using 2- (4-nitrophenyl)ethyl mthylene-bis(phosphonate) as the phosphonylating agent
AU - Lesiak, Krystyna
AU - Watanabe, Kyoichi A.
AU - Pankiewicz, Krzysztof W.
PY - 1998/1/1
Y1 - 1998/1/1
N2 - 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, which in reaction with suitably protected 2'- deoxynucleosides 3 gave P1,P2-disubstituted methylenebis(phosphonate)s 4. Removal of the nitrophenylethyl group by β-elimination with DBU afforded the corresponding 2'-deoxynucleoside 5'-methylene-bis(phosphonate) analogues 5.
AB - 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, which in reaction with suitably protected 2'- deoxynucleosides 3 gave P1,P2-disubstituted methylenebis(phosphonate)s 4. Removal of the nitrophenylethyl group by β-elimination with DBU afforded the corresponding 2'-deoxynucleoside 5'-methylene-bis(phosphonate) analogues 5.
UR - http://www.scopus.com/inward/record.url?scp=0031728665&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0031728665&partnerID=8YFLogxK
U2 - 10.1080/07328319808004723
DO - 10.1080/07328319808004723
M3 - Article
AN - SCOPUS:0031728665
SN - 0732-8311
VL - 17
SP - 1857
EP - 1860
JO - Nucleosides and Nucleotides
JF - Nucleosides and Nucleotides
IS - 9-11
ER -