Method for preparation of pentopyranosyl nucleosides
Title compds. consisting of ribo-, arabino-, xylo-, or lyxo-pyranoses in place of the usual ribo-furanose, were prepd. and used in solid-phase synthesis to construct (b-D-ribo)-(4'->2')-H-GGGCGGGC-H(I). Thus, 1,2,3,4-tetra-O-benzoyl-a/b-D-ribo-pyranose was substituted at the 1-position with a series of protected nucleoside bases, and the sugar manipulated through a series of steps to give either the 4'-O-dimethoxytrityl-3'-O-benzoyl-2'-O-(allyloxy)(diisopropyl-amino)phosphine compds. suitable for solid-phase synthesis of oligonucleotides, or 2'-O-CO(CH2)5CO2H compds. suitable for attachment to amine-resins to form the initial base of a growing chain. A key step in this synthesis was the simultaneous protection of 3'- and 4'-O by reaction with an aldehyde, ketone, acetal, or ketal protecting group to form cyclic acetals. These intermediates were then used in the construction of I. [on SciFinder (R)]
7864082
Alternative title(s) : (de) Verfahren zur herstellung von pentopyranosyl-nucleosiden (fr) Procede de preparation de pentopyranosyle-nucleotides (en) Method for the production of pentopyranosyl nucleosides
Patent number | Country code | Kind code | Date issued |
DE59908585 | DE | D1 | 2004-03-25 |
AT259824 | AT | T | 2004-03-15 |
EP1070079 | EP | B1 | 2004-02-18 |
US6545134 | US | B1 | 2003-04-08 |
AU755533 | AU | B2 | 2002-12-12 |
JP2002511479 | JP | A | 2002-04-16 |
KR20010074475 | KR | A | 2001-08-04 |
EP1070079 | EP | A2 | 2001-01-24 |
BR9909909 | BR | A | 2000-12-26 |
WO9952923 | WO | A3 | 2000-01-13 |
AU3706499 | AU | A | 1999-11-01 |
CA2327436 | CA | A1 | 1999-10-21 |
WO9952923 | WO | A2 | 1999-10-21 |
DE19815901 | DE | A1 | 1999-10-14 |