Efficient syntheses of l-ribose and 2-deoxy l-ribose from d-ribose and l-arabinose
โ Scribed by Michael E. Jung; Yue Xu
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 204 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
Interconversion of the ends of D-ribese 2 afforded in 6 steps and 45% overall yield L-ribose 1, from which 2-deoxy L-ribose 12 was easily prepared. In addition, the inexpensive L-arabinose 13 was also converted into 2-deoxy L-ribose 12 via a reductive radical rearrangement of the arabinopyranosyl bromide 14.
๐ SIMILAR VOLUMES
We report herein the total synthe.ses of 2-deoxy-DL-and L-rlboses. As Illustrated in the following scheme, the Reformatsky reaction of ethyl bromoaoetate with aoroleln afforded the p-hydroxy eater (I) in a yield of 40-502, whloh was hydrolysed by means of aqueous potassium hydroxide to give the DL-a
A practical synthesis of 2-deoxy-L-ribose from L-arabinose depends on the efficient reduction by iodide of a triflate a to a lactone. The X-ray crystal structure of 3,4-O-isopropylidene-L-arabinono-1,5-lactone is reported.