Impressive progress has been made in the construction of O-glycosides from 1-thioglycosides [1], and methods have been developed for the preparation of 1-thioglycosides (5-8) from acetylated glycosyl halides (1) (Scheme 1) [2-3], acetylated glycosides (2) [4][5][6][7], and methyl glycosides (3) [8].
Nucleoside synthesis from thioglycosides
β Scribed by Spencer Knapp; Wen-Chung Shieh
- Publisher
- Elsevier Science
- Year
- 1991
- Tongue
- French
- Weight
- 263 KB
- Volume
- 32
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Acetylated phenyl and methyl I-thiofurano-and pyranosides react with blylated urocil, acetylcytosine, and benzoyladenine under the influence ofNIS I trij'lic acid to generate the j%nucleoside derivatives in good yield.
π SIMILAR VOLUMES
Bicyclic (2-oxapyrrolizidines) and monocyclic (piperidine) azasugar ethyl thioglycosides, a new type of azasugar derivative, are stereoselectively prepared from suitable glycosylenamines, through anhydroazasugar derivatives.
The one pot conversion of 1,2,4,6-tetra-O-acetyl-B-D\_glucopyranose, 1, into phenyl 2,4,6-tri-0-acetyl-3-0-trialkylsilyl-l-thio-~-~-glucopyranosides, 3, is described. The method is applicable to use with galactopyranosyl-, 2-deoxyglucopyranosyl-, and ribofuranosyl-starting materials.
A method to form glycosyl linkages between nitrogen-containing heterocycles and appropriately protected furanoses is described. The method is highly beta-selective, operationally simple, and utilizes readily available reagents making the process amenable to scaleup. Representative examples of coupli