ChemInform Abstract: Preparation of Acetylated 1-Fluoroglycopyranosyl Cyanides.
✍ Scribed by V. GYOLLAI; L. SOMSAK; Z. GYOERGYDEAK
- Book ID
- 101876038
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 33 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Preparation of Acetylated 1-Fluoroglycopyranosyl Cyanides.
-Reaction of 1-chloro-or 1-bromoglycopyranosyl cyanides (I), (V), and (VI) with silver fluoride or silver tetrafluoroborate represents a convenient method for the synthesis of 1-fluoroglycopyranosyl cyanides. It is shown that reaction with silver fluoride proceeds by S N 2 substitution with electrophilic assistance of silver ions by inversion of the configuration at the anomeric carbon. In contrast, reaction with silver tetrafluoroborate proceeds with retention of the anomeric configuration.
📜 SIMILAR VOLUMES
Iodine as Acetylation Catalyst in the Preparation of 1,1-Diacetates from Aldehydes. -The title reaction proceeds for a variety of aldehydes with shorter reaction times and higher yields as with usually applied catalysts and represents a general method for the synthesis of acylals (III) or diacylals