Journal
SYNTHESIS-STUTTGART
Volume -, Issue 22, Pages 3827-3834Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0030-1258270
Keywords
nucleosides; blocking group stability; tetraisopropyl-disiloxane-1; 3-diyl; protecting group; N-deacylation; O-deacylation
Categories
Funding
- Russian Foundation for Basic Research
- Russian Academy of Sciences
Ask authors/readers for more resources
The stability of tetraisopropyldisiloxane-1,3-diyl (TIPDS) protection in nucleosides in ammonia/amine solutions in methanol and ethanol was studied. In ammonia-methanol at ambient temperature significant partial cleavage of TIPDS was observed. When ethanol was used instead of methanol this undesired side reaction was completely inhibited. It was found that commercially available 8 M methylamine-ethanol solution is the reagent of choice for selective deacylation of N- or/and O-acyl protected nucleosides without notable cleavage of 3',5'-TIPDS group. Several examples of the developed protocol for the preparation 2'-O-modified nucleosides with overall high yields are presented.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available