Synthesis of densely functionalised C-glycosides by a tandem oxy Michael addition-Wittig olefination pathway.
Wittig olefination of 5,6-dideoxy-5,6-anhydro-6-nitro-D-glucofuranose (5) triggered a concomitant cyclisation via oxy Michael addition of the C2-hydroxyl group resulting in the formation of C-vinyl glycosides with Z-olefinic geometry.
Senthil Kumar
R
R
Organic Chemistry Division, Central Leather Research Institute, Chennai, India.
Karthikeyan
K
K
Phani Kumar
B V N
BV
Muralidharan
D
D
Perumal
P T
PT
D000475:Alkenes / Q000737:chemistry*; D006027:Glycosides; D008956:Models, Chemical; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis / Q000737:chemistry
D000475:Alkenes; C438934:C-glycoside; D006027:Glycosides; D009005:Monosaccharides; D014753:Vinyl Compounds