7-DEAZAGUANOSINE - PHOSPHORAMIDITE AND PHOSPHONATE BUILDING-BLOCKS FOR SOLID-PHASE OLIGORIBONUCLEOTIDE SYNTHESIS

Autor(en): SEELA, F
MERSMANN, K
Stichwörter: CHEMICAL SYNTHESIS; Chemistry; Chemistry, Organic; NUCLEOSIDE
Erscheinungsdatum: 1992
Herausgeber: PERGAMON-ELSEVIER SCIENCE LTD
Journal: HETEROCYCLES
Volumen: 34
Ausgabe: 2
Startseite: 229
Seitenende: 236
Zusammenfassung: 
The synthesis of oligoribonucleotide building blocks (phosphonates and phosphoramidites) of 7-deazaguanosine (2-amino-7-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one , 1) is described. Silylation of the 2'-hydroxy group of 7-deaza-N2-isobutyryl-5'-0-(4-monomethoxytrityl)guanosine (5) was studied with regard to the 2'-selectivity. Best results were obtained with triisopropylsilyl chloride/AgNO3. The 2'-0-protected intermediates (6a and 6b) were converted into the phosphonates (3a, b) or methylphosphoramidites (4a, b), which were successfully used for solid-phase oligoribonucleotide synthesis of (c7G-C)3 (9).
ISSN: 03855414
DOI: 10.3987/COM-91-9515

Show full item record

Page view(s)

12
Last Week
0
Last month
1
checked on Feb 23, 2024

Google ScholarTM

Check

Altmetric