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Efficient syntheses of l-ribose and 2-deoxy l-ribose from d-ribose and l-arabinose

โœ 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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โœฆ 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.


๐Ÿ“œ SIMILAR VOLUMES


The total syntheses of 2-deoxy-DL- and L
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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

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โœ Alistair J. Stewart; Richard M. Evans; Alexander C. Weymouth-Wilson; Andrew R. C ๐Ÿ“‚ Article ๐Ÿ“… 2002 ๐Ÿ› Elsevier Science ๐ŸŒ English โš– 219 KB

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.