Studies on stereospecific formation of P-chiral internucleotide linkage

Autor: Zbigniew J. Leśnikowski, Anna Sibińska
Rok vydání: 1986
Předmět:
Zdroj: Tetrahedron. 42:5025-5034
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)88054-6
Popis: Substitution of 4-nitrophenoxy group at phosphorus atom of 5'-O-monomethoxytrityl-2'-deoxyadenosine 3'-O-¦ O-(4-nitrophenyl)-S-methyl-phosphorothioate¦( 4 )¦(Sp)- 4 : (Rp)- 4 =90:10 and (Sp)- 4 :(Rp)- 4 =30:70¦by base-activated 5'-hydroxyl function of 3'-O-tert-butyldimethylsilyl-2'-deoxyadenosine ( 5 ) gives fully protected P-chiral 2'-deoxyadenylyl(3',5') 2'-deoxyadenosine S-methylphosphorothioates ( 6 ), ¦(Sp)- 6 :(Rp)- 6 =92:8 and (Sp)- 6 :(Rp)- 6 -32:68 respectively ¦.Demethylation of internucleotide S-methylphosphorothioate group in 6 and deprotection of 3'- and 5'-hydroxyl functions lead to diastereoisomeric mixture of 2'-deoxyadenylyl (3',5') 2'-deoxyadenosine-O, O-phosphorothioates ( 7 ).
Databáze: OpenAIRE