Abstract
Thermolytic cleavage of 3′-OH protected thymidine is the most common method of preparing furanoid glycals. We have observed that glycosidic bond cleavage is more facile when the 5-OH of thymidine was also protected with a silyl group. Addition of trimethylsilyl chloride facilitated cleavage of the glycosidic bond; thus, both modifications are required for the formation of the furanoid glycal. Investigations into the selective deprotection of 5′-silyl versus 3′-silyl and subsequent glycosidic bond cleavage are reported herein.
Original language | English (US) |
---|---|
Pages (from-to) | 319-327 |
Number of pages | 9 |
Journal | Nucleosides, Nucleotides and Nucleic Acids |
Volume | 31 |
Issue number | 4 |
DOIs | |
State | Published - Apr 1 2012 |
Externally published | Yes |
Keywords
- C-nucleosides
- Furanoid glycal
ASJC Scopus subject areas
- Biochemistry
- Molecular Medicine
- Genetics