A FACILE SYNTHESIS OF THE PHOSPHORAMIDITES OF 2-N-METHYL-2'-DEOXY (OR2'-O-ALLYL)-PSI-ISOCYTIDINE, 1,3-DIMETHYL-2'-DEOXY-PSI-URIDINE AND N1-METHYL-2'-O-ALLYL-PSI-URIDINE AS SYNTHONS SUITABLE FOR OLIGONUCLEOTIDE SYNTHESIS

Authors
BHATTACHARYA BK REVANKAR GR
Citation
Bk. Bhattacharya et Gr. Revankar, A FACILE SYNTHESIS OF THE PHOSPHORAMIDITES OF 2-N-METHYL-2'-DEOXY (OR2'-O-ALLYL)-PSI-ISOCYTIDINE, 1,3-DIMETHYL-2'-DEOXY-PSI-URIDINE AND N1-METHYL-2'-O-ALLYL-PSI-URIDINE AS SYNTHONS SUITABLE FOR OLIGONUCLEOTIDE SYNTHESIS, Nucleosides & nucleotides, 13(8), 1994, pp. 1721-1738
Citations number
41
Categorie Soggetti
Biology
Journal title
Nucleosides & nucleotides → ACNP
ISSN journal
07328311
Volume
13
Issue
8
Year of publication
1994
Pages
1721 - 1738
Database
ISI
SICI code
0732-8311(1994)13:8<1721:AFSOTP>2.0.ZU;2-4
Abstract
An efficient and facile syntheses of 5'-O-(4,4'-dimethoxytrityl)-3'-[2 -cyanoethyl bis(1-methylethyl)]phosphoramidites of 2-N-methyl-2'-deoxy -psi-isocytidine (h), 2-N-methyl-2'-deoxy-alpha-psi-isocytidine (13 ), 2-N-methyl-2'-O-allyl-psi-isocytidine (11), 1,3-dimethyl-2'-deoxy-psi -uridine (4) and N1-methyl-2'-O-allyl-psi-uridine (19) have been accom plished in good overall yields. The pyrimidine-pyrimidine transformati on reaction was found to be useful for the preparation of 2-N-methyl-2 '-O-allyl-psi-isocytidine (10). The utility of these novel phosphorami dites is demonstrated by their incorporation into oligonucleotides via solid-support, oligonucleotide methodology.