107911-44-4Relevant articles and documents
Completely β-selective glycosylation using 3,6- O-(o-xylylene)-bridged axial-rich glucosyl fluoride
Okada, Yasunori,Asakura, Noriaki,Bando, Masafumi,Ashikaga, Yoshiki,Yamada, Hidetoshi
, p. 6940 - 6943 (2012/06/15)
A completely β-selective glycosylation that does not rely on neighboring group participation is described. The novelty of this work is the design of the glycosyl donor locked into the axial-rich form by the o-xylylene bridge between the 3-O and 6-O of d-glucopyranose. The synthesized 2,4-di-O-benzyl-3,6-O-(o-xylyene)glucopyranosyl fluoride could efficiently react with various alcohols in a SnCl2-AgB(C6F 5)4 catalytic system. The mechanism composed of the glycosylation and isomerization cycles was revealed through comparative experiments using acidic and basic molecular sieves. The achieved perfect stereocontrol is attributed to the synergy of the axial-rich conformation and convergent isomerization caused by HB(C6F5)4 generated in situ.
How the arming participating moieties can broaden the scope of chemoselective oligosaccharide synthesis by allowing the inverse armed-disarmed approach
Smoot, James T.,Demchenko, Alexei V.
experimental part, p. 8838 - 8850 (2009/04/05)
(Chemical Equation Presented) A new method for stereocontrolled glycosylation and chemoselective oligosaccharide synthesis has been developed. It has been determined that complete 1,2-trans selectivity can be achieved with the use of a 2-O-picolyl moiety,
Removal of benzyl protecting groups from controlled pore glass linked sugars
Adinolfi, Matteo,Barone, Gaspare,Iadonisi, Alfonso,Schiattarella, Marialuisa
, p. 5971 - 5972 (2007/10/03)
Removal of benzyl protecting groups from controlled pore glass bound monosaccharides can be performed with the NaBrO3/Na2S2O4 system in ethyl acetate/water.
