6743-64-2Relevant academic research and scientific papers
Organocatalyzed direct glycosylation of unprotected and unactivated carbohydrates
Schmalisch, Sebastian,Mahrwald, Rainer
supporting information, p. 5854 - 5857 (2013/12/04)
Organocatalyzed direct glycosylation of unprotected and unactivated carbohydrates is reported. This process is catalyzed by triphenylphosphine and tetrabromomethane at room temperature under neutral conditions. With this operationally simple protocol thermodynamically favored, glycosides were obtained in a very straightforward reaction.
Direct glycosylation of unprotected and unactivated carbohydrates under mild conditions
Pfaffe, Matthias,Mahrwald, Rainer
supporting information; experimental part, p. 792 - 795 (2012/05/04)
Ligand exchange acetalization of acetals in the presence of catalytic amounts of mandelic acid and titanium tert-butoxide is reported. This transformation is successfully extended to glycosylation of unprotected and unactivated pentoses. Even unreactive pentoses such as d-arabinose or d-lyxose can be transformed by this new methodology into corresponding isopropyl glycosides.
Enzymatic Synthesis of Alkyl β-Xylosides from Xylobiose by Application of the Transxylosyl Reaction of Aspergillus niger β-Xylosidase
Shinoyama, Hirofumi,Kamiyama, Yoshi,Yasui, Tsuneo
, p. 2197 - 2202 (2007/10/02)
The enzymatic synthesis of alkyl β-xylosides from xylobiose and alcohols through the transxylosyl reaction of Aspergillus niger IFO 6662 enzyme was studied.Various alkyl β-xylosides were effectively synthesized from xylobiose and water miscible alcohols such as methanol, ethanol, 1-propanol and 2-propanol.The molar ratios of the products, respective β-xylosides and xylose, were approximately 1:1, indicating a theoretical yield for the transfer reaction.Various water insoluble alcohols, such as 1-butanol, 1-pentanol, 1-hexanol, benzyl alcohol and 2-butanol, were also acted as effective acceptors for the transxylosyl reaction, where a great part of the synthesized β-xylosides was found in the insoluble alcohol layer, only xylose and a trace of xylobiose being found in the water layer.Therefore, the synthesized β-xylosides, such as 1-hexyl β-xyloside, could be readily separated from the reaction mixture and crystallized after evaporation of the insoluble alcohol.
