Synthesis of natural/13C-enriched d-tagatose from natural/13C-enriched d-fructose
| Autor: | Adam J. Shuhendler, Thomas A. Charlton, Mojmír Suchý, Robert N. Ben |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
D-tagatose
010405 organic chemistry Organic Chemistry D fructose Periodinane Fructose General Medicine 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Analytical Chemistry chemistry.chemical_compound chemistry Yield (chemistry) Organic chemistry Epimer Ketohexose Tagatose |
| Zdroj: | Carbohydrate Research. 507:108377 |
| ISSN: | 0008-6215 |
| DOI: | 10.1016/j.carres.2021.108377 |
| Popis: | A concise, easily scalable synthesis of a rare ketohexose, d -tagatose, was developed, that is compatible with the preparation of d -[UL-13C6]tagatose. Epimerization of the widely available and inexpensive ketohexose d -fructose at the C-4 position via an oxidation/reduction (Dess-Martin periodinane/NaBH4) was a key step in the synthesis. Overall, fully protected natural d -tagatose (3.21 g) was prepared from d -fructose (9 g) on a 50 mmol scale in 23% overall yield, after five steps and two chromatographic purifications. d -[UL-13C6]Tagatose (92 mg) was prepared from d -[UL-13C6]fructose (465 mg, 2.5 mmol) in 16% overall yield after six steps and four chromatographic purifications. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect