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Electrophilic addition to 4-thio furanoid glycal: a highly stereoselective entry to 2′-deoxy-4′-thio pyrimidine nucleosides

✍ Scribed by Kazuhiro Haraguchi; Ayako Nishikawa; Eiko Sasakura; Hiromichi Tanaka; Kazuo T. Nakamura; Tadashi Miyasaka

Book ID
104259183
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
222 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

4-Thio furanoid glycals with different types of O-silyl protection have been prepared from benzyl 3,5-di-O-benzyl-2-deoxy-l,4-dithio-D-erythro-pentofumnoside. Face-selectivity for PhSeCI-or N-iodosuecimide-initiated addition of a pyrimidine base to the thioglycal was found to be controlled by O-silyl protecting groups. Using the thioglycal protected with a 3,5-O-di-t-hutylsilyl group, a highly stereoselective synthesis of ~-2'-deoxy-4'-thio pyrimidine nucleosides has been accomplished.

📜 SIMILAR VOLUMES

ChemInform Abstract: Electrophilic Addit
ChemInform Abstract: Electrophilic Addition to 4-Thio Furanoid Glycal: A Highly Stereoselective Entry to 2′-Deoxy-4′-thio Pyrimidine Nucleosides.
✍ K. HARAGUCHI; A. NISHIKAWA; E. SASAKURA; H. TANAKA; K. T. NAKAMURA; T. MIYASAKA 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 38 KB

Three 4-thio furanoid glycals (III) and (V) are synthesized and converted stereoselectively to pyrimidine nucleosides, e.g. (VIII)-(X). In addition, (Xb) is reduced to give the corresponding 2'-deoxy derivative (XI) which shows activity against herpes virus.