98750-48-2Relevant academic research and scientific papers
Branched-chain Sugars. Part 17. A Synthesis of L-Rubranitrose (2,3,6-Trideoxy-3-C-methyl-4-O-methyl-3-nitro-L-xylo-hexopyranose)
Brimacombe, John S.,Rahman, Khandker M. M.
, p. 1067 - 1072 (2007/10/02)
L-Rubranitrose (2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitro-L-xylo-hexopyranose) (4) has been elaborated from methyl 3-acetamido-2,3,6-trideoxy-3-C-methyl-α-L-xylo-hexopyranoside (27).N-Deacetylation of the corresponding 4-O-methyl derivative (26), with calcium in liquid ammonia, afforded the amino sugar (25), which was then oxidised to methyl 2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitro-α-L-xylo-hexopyranoside (28).Acidic hydrolysis of the latter compound gave L-rubranitrose (4), which proved to be enantiomeric with the novel methyl-branched nitro sugar found in the antibiotic rubradirin.In another approach to L-rubranitrose (4), methyl 2,6-dideoxy-4-O-methyl-α-L-threo-hexopyranosid-3-ulose (11) was shown to react with cyanide ion under equilibrating conditions to give methyl 3-C-cyano-2,6-dideoxy-4-O-methyl-α-L-xylo-hexopyranoside (12), whereas the corresponding L-lyxo cyanohydrin (22) is the kinetically favoured product.
