Studies on the construction of glycosidic linkage in guanofosfocins. Glycosylation of 8-oxoinosine and 8-oxoguanosine derivatives with mannopyranosyl bromide
✍ Scribed by Hideyuki Sugimura; Yumiko Natsui
- Book ID
- 104253717
- Publisher
- Elsevier Science
- Year
- 2003
- Tongue
- French
- Weight
- 161 KB
- Volume
- 44
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
In model studies directed to the total synthesis of guanofosfocins, a unique glycosydic bond formation between the 8-oxoinosine derivatives and mannopyranosyl donor is described. The reaction employing previously reported conditions resulted in the formation of two regioisomers, the 8-O-and N7-mannosylated inosine derivatives. However, the use of tetrabutylammonium iodide as a catalyst was found to improve the chemoselectivity towards O-glycosylation to afford the desired 8-O-mannosylated products in satisfactory yields. The established procedure was successfully applied for the synthesis of 8-(mannopyranosyloxy)guanosine derivative.