Synthesis of Analogues of 1-(2‘, 3’-Dideoxy-β-D-glyceropent-2-enofuranosyl)thymine
✍ Scribed by G. FONTAINE; C. LEQUENNE; C. FOSSEY; M. RENOUD-GRAPPIN; D. LADUREE
- Book ID
- 118110718
- Publisher
- Pharmaceutical Press
- Year
- 1998
- Tongue
- English
- Weight
- 552 KB
- Volume
- 4
- Category
- Article
- ISSN
- 2042-7158
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1-(2-O-Acetyl-3,5,6-tri-O-benzoyl-beta-D-glucofuranosyl)thymine (1) was converted into the 2,2'-anhydro derivative 4 by selective deacetylation, mesylation, and treatment with 1,8-diazabicyclo[5.4.0]undec-7-ene. Cleavage of the 2,2'-anhydro ring in 4 with hydrogen bromide or hydrogen chloride led to
## Abstract Free radicals generated by reaction of protected methyl 2,3‐ dideoxy‐3‐iodopentofuranosides 2, 3, and 9 with tributyltin hydride in the presence of a radical initiator (AIBN) were treated with acrolein to give methyl 2,3‐dideoxy‐3‐(3‐oxopropyl)pentofuranosides 4 and 5. Reduction of 5 wi