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 br
2-Deoxy-l-ribose from an l-arabinono-1,5-lactone
β Scribed by Alistair J. Stewart; Richard M. Evans; Alexander C. Weymouth-Wilson; Andrew R. Cowley; David J. Watkin; George W.J. Fleet
- Publisher
- Elsevier Science
- Year
- 2002
- Tongue
- English
- Weight
- 219 KB
- Volume
- 13
- Category
- Article
- ISSN
- 0957-4166
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β¦ Synopsis
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.
π SIMILAR VOLUMES
The relative configuration at C-2 of 2,4-dimethyl-3,4-__O__-isopropylidene-L-arabinono lactone, C~10~H~16~O~5~, which exists in the boat form, was unequivocally established by X-ray crystallographic analysis. The absolute configuration was determined by the use of 2-__C__-methyl-D-ribonolactone as a
The relative configuration of the title lactone, C 10 H 15 N 3 O 4 , a compound of value in the synthesis of complex pyrrolidines, was determined by X-ray crystallographic analysis.