18794-74-6Relevant articles and documents
Efficient assembly of oligomannosides using the hydrophobically assisted switching phase method
Meng, Shuai,Tian, Tian,Han, Dong,Wang, Lin-Na,Tang, Shao-Geng,Meng, Xiang-Bao,Li, Zhong-Jun
supporting information, p. 6711 - 6722 (2015/06/25)
The hydrophobically assisted switching phase (HASP) method was applied in the assembly of oligomannosides. A new mannosyl donor with high reactivity was selected after a series of optimization studies, which was suitable for the synthesis of oligomannosides via the HASP method. The practicability of the HASP method towards the synthesis of branched oligosaccharides was explored and two branched penta-mannosides were assembled efficiently.
Hydrophobically assisted switching phase synthesis: The flexible combination of solid-phase and solution-phase reactions employed for oligosaccharide preparation
Bauer, Joerg,Rademann, Joerg
, p. 7296 - 7297 (2007/10/03)
Hydrophobically assisted switching phase (HASP) synthesis is a concept that allows the choice between the advantages of solid-supported chemistry and those of solution-phase synthesis. Starting from the examination of adsorption and desorption properties of hydrophobic molecules to and from reversed-phase silica, we designed a dilipid as a quantitative and fully reversible HASP anchor, permitting final product release. The utility of this new tool in synthetic organic chemistry was demonstrated on oligosaccharide preparation. The synthesis of a pentarhamnoside was accomplished by repetitive glycosylation reactions. Glycosylations were conducted preferably in solution, whereas all protecting group manipulations were performed on solid support. Without the need for chromatographic purification of intermediates, the HASP system furnished the final product after 12 linear steps with average yields of 94% per step at a scale of 0.1 mmol, thus overcoming several of the limitations encountered in the solid-phase synthesis of complex carbohydrates. Copyright
Synthesis of 1,3-di-O-alkyl-2-O-(β-glycosyl)glycerols bearing oligosaccharides as hydrophilic groups
Minamikawa, Hiroyuki,Murakami, Teiichi,Hato, Masakatsu
, p. 111 - 118 (2007/10/02)
A novel series of synthetic glycolipids, 1,3-di-O-alkyl-2-O-(β-glycosyl)glycerols, and their efficient synthetic route were proposed.These glyceroglycolipids were synthesized in good overall yields and stereoselectivity in five steps via trichloroacetimidate glycosylation with 1,3-di-O-alkylglycerols.This route was applied to prepare the glycolipids bearing a cello- or malto-oligosaccharide with a definite number of sugar residues from one to six.Thin-layer chromatography, elemental analysis, nuclear magnetic resonance spectroscopy and infrared absorption spectroscopy confirmed that these glycolipids were chemically pure compounds.Keywords: Glyceroglycolipids; Oligosaccharide headgroups; Synthesis
