865093-44-3Relevant academic research and scientific papers
Synthesis and conformational studies on methyl 4-O-acetyl-3-azido-2,3,6- trideoxy-hex-5-enopyranosides of the L series
Liberek, Beata
, p. 2039 - 2047 (2005)
Methyl 3-azido-2,3-dideoxy-α-D-xylo-, -α-D-lyxo-, and -β-D-xylo-hexopyranosides were converted into 4-O-acetyl-3-azido-6-iodo-2, 3,6-trideoxy analogues via 6-O-p-tolylsulfonyl compounds. The elimination of hydrogen iodide from 6-iodo glycosides yielded methyl 4-O-acetyl-3-azido-2,3,6- trideoxy-β-L-erythro-, -α-L-threo-, and -β-L-threo-hex-5- enopyranosides. The configuration and conformation of all products are evaluated in depth on the basis of 1H and 13C NMR data. Factors determining conformational energy in 4-O-protected-3-azido-2,3,6,-trideoxy-hex- 5-enopyranosides are discussed.
