172360-96-2Relevant academic research and scientific papers
DDQ-mediated oxidation of 4,6-O-methoxybenzylidene-protected saccharides in the presence of various nucleophiles: Formation of 4-OH, 6-Cl, and 6-Br derivatives
Zhang, Zhiyuan,Magnusson, Goeran
, p. 2394 - 2400 (2007/10/03)
Treatment of 4,6-O-p-methoxybenzylidene-protected pyranosidic mono- and disaccharides with 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), in the presence of a few equivalents of water, gave the corresponding 6- and 4-O-p-methoxybenzoates with unprotected hydroxyl groups in the 4- and 6-position in the ratio ~4:1 and in 85-98% yield. Dry conditions in the presence of halide salts gave the 6-deoxychloro and -bromo 4-O-p-methoxybenzoates exclusively, in >90% yield.
Synthesis of Double-Chain Bis-sulfone Neoglycolipids of the 2'-, 3'-, and 6'-Deoxyglobotrioses
Zhang, Zhiyuan,Magnusson, Goeran
, p. 7304 - 7315 (2007/10/03)
Partially protected 2-(trimethylsilyl)ethyl deoxylactosides (deoxygenated in the 2-, 3-, and 6-positions of the galactose unit) were synthesized via various routes and glycosylated with galactosyl donors to give the corresponding deoxytrisaccharides.Removal of the protecting groups gave the 2-(trimethylsilyl)ethyl 2'-, 3'-, and 6'-deoxyglobotriosides.Transformation of the protected trisaccharides into trichloroacetimidates, via the corresponding hemiacetals, proceeded in 86 - 96percent overall yield.Glycosylation of 3-(hexadecylsulfonyl)-2-propanol with the trisaccharidic trichloroacetimidates, in 37 - 68percent yield, followed by removal of protecting groups, gave the title neoglycolipids.
