Electroorganic Synthesis, 62!! Anodic Heterocoupling (Mixed Kolbe Electrolysis) of Carbohydrate Carboxylic Acids with Alkanoic Acids to C-Glycosides
✍ Scribed by Harenbrock, Michael ;Matzeit, Agnes ;Schäfer, Hans J.
- Publisher
- John Wiley and Sons
- Year
- 2006
- Tongue
- English
- Weight
- 943 KB
- Volume
- 1996
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Abstract
2‐Deoxy carbohydrate carboxylic acids 1–3 were prepared from glucal 4, acetobromoglucose 5, and D‐galactose (7), respectively. The acids 1–3 were electrolyzed with different coacids at controlled current in methanol at platinum electrodes in an undivided cell to afford C‐glycosides as heterocoupling products in 46–70% yield. Compound 28, obtained by deacylation of 17, has a critical micelle concentration (cmc) of 2.4 mM, which is about 2.5 times lower than that of the corresponding O‐glycoside 29. Compound 28 forms liquid crystals with a smectic A phase in the range between 96 and 190°C, which is twice as large as that of 29. Compounds 31 and 32, obtained by deprotection of 23 and 24, respectively, also exhibit liquid crystalline behavior.