A general route to 4-C-branched sugars. Synthesis of methyl alpha-caryophylloside.
The total synthesis of methyl 3,6-dideoxy-4-C-(D-altro-1,3,4,5 tetrahydroxyhexyl)-alpha-D-xylo-hexopyranoside, the methyl glycoside of the recently isolated 4-C-branched sugar caryophyllose, has been completed in a stereoselective and convergent manner. The synthesis of this dodecose relies on the diiodosamarium mediated coupling of two six-carbon fragments: a cyclic ketone and an acid chloride.
Prandi
J
J
Institut de Pharmacologie et de Biologie Structurale du CNRS, 205 route de Narbonne, F-31077, Toulouse, France. prandi@ipbs.fr
D006027:Glycosides / Q000138:chemical synthesis; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D010935:Plant Diseases / Q000382:microbiology; D011549:Pseudomonas / Q000737:chemistry; D013237:Stereoisomerism
D006027:Glycosides; D009005:Monosaccharides; C439355:methyl -caryophylloside