1, 1, 3, 3-Tetraisopropyl-3-(2-(triphenylmethoxy)ethoxy)disiloxane-1-yl group, a potential 5′-O-protecting group for solid-phase RNA synthesis
✍ Scribed by Ichiro Hirao; Masahiro Koizumi; Yoshiharu Ishido; Alex Andrus
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 239 KB
- Volume
- 39
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
1, 1, 3, 3-Tetraisopmpyl-3-(2-(triphenylmcthoxy)ethoxy)disiloxane-l-yl (TES) group was designed for solid-phase RNA synthesis as a 5'-O-protecting group, which can be combined with the tetrahydropyranyl group, a 2'-hydroxyl protecting group. The TES group can be selectively introduced to the 5'-hydroxy group ofnucleosides and can be easily removed by 0.1M tetrabutyl~amonium fluoride or 0.01M hydrochloric acid.
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Treatment of benzyl O-/?-n-galactopyranosyl-( 1+3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-j3-D-glucopyranoside with tert-butylchlorodiphenylsiiane afforded the 6'-0-tert-butyldiphenylsilyl ether, which was converted into the 3',4'-0-isopropylidene derivative. Methylation and subsequent removal of