5204-98-8Relevant academic research and scientific papers
A unique synthetic method to convert a D-sugar into 2-deoxy-L-ribitol through carbonyl translocation
Hsu, Nai-Yun,Chang, Che-Chien
, p. 658 - 661 (2013)
A unique and highly efficient radical process was developed to prepare 2-deoxy-L-ribitol. The radical cyclization precursor was prepared over several steps from D-sugars. Radical cyclization followed by fragmentation gave exclusively the desired product, with carbonyl translocation in an acyclic carbohydrate system. The radical process was optimized to avoid the formation of byproducts. The reaction mechanism was studied by the concentration effect, which indicated that both the radical cyclization and the fragmentation steps are relatively rapid. The stereochemistry of the 2-deoxy-L-ribitol was confirmed by X-ray crystal structure. By using this synthetic approach, a D-sugar derivative could be transformed into 2-deoxy-L-ribose in a single radical reaction. A unique and highly efficient radical process (complete within minutes) was developed to prepare of 2-deoxy-L-ribitol. Radical cyclization followed by fragmentation gave exclusively the desired product, with carbonyl translocation in an acyclic carbohydrate system. By using this synthetic approach, a D-sugar derivative could be transformed into a 2-deoxy-L-sugar in a single radical reaction. Copyright
New Polyketide Metabolites from Aspergillus melleus: Structural and Stereochemical Studies
Garson, Mary J.,Staunton, James,Jones, Peter G.
, p. 1021 - 1026 (2007/10/02)
The structures of two new fungal products asperlactone (5) and isoasperlactone (6) have been deduced by comparison of their spectroscopic data with that of aspyrone (3), a known co-metabolite.All three compounds have been degraded by ozonolysis to produce crystalline derivatives of 2,3-epoxybutyric acid (9) and 1-methylglycerol (11).From measurements of optical activity it has been established that aspyrone and isoasperlactone have the (5S,6R,8S,9S) configuration, whereas that of asperlactone is (5R,6S,8S,9S).The relative stereochemistry of aspyrone has been checked by an X-ray crystallographic study: 12121, a=4.427(3), b=14.272(3), c=14.968(3) Angstroem, Z=4, R=0.033 for 1131 unique observed reflections>.The stereochemical relationships are discussed in terms of a biosynthetic proposal by which (3) and (5) would be biosynthesised from a common intermediate via alternative cyclisations of a carboxy group onto an epoxide residue.It is possible that (6) is a chemical artefact derived from (3).
