Primary and secondary alcohols are efficiently converted to the halides under neutral conditions.
β¦ LIBER β¦
Preparation of glycosyl halides under neutral conditions
β Scribed by Beat Ernst; Tammo Winkler
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- French
- Weight
- 216 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
β¦ Synopsis
The anomeric hydroxyl group of various furanose andpyranose hemiacetals can be replaced by a fluorine, chlorine, bromine or iodine atom under neutral conditions using haloenamines.
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Glycosyl phosphites 1-3 derived from glucose are activated under neutral conditions and without the addition of any further promoter in 1 M solutions of LiClO 4 , Mg(ClO 4 ) 2 or Ba(ClO 4 ) 2 in ether, CH 2 Cl 2 , or CH 3 CN and react under these conditions with the alcohols 5-9 to give the glycosid