897364-02-2Relevant articles and documents
Neighboring-group participation by C-2 ether functions in glycosylations directed by nitrile solvents
Chao, Chin-Sheng,Lin, Ching-Yu,Mulani, Shaheen,Hung, Wei-Cheng,Mong, Kwok-Kong Tony
supporting information; experimental part, p. 12193 - 12202 (2011/12/01)
Ether-protecting functions at C-2 hydroxy groups have been found to play participating roles in glycosylations when the reactions are conducted in nitrile solvent mixtures. The participation mechanism is based on intramolecular interaction between the lone electron pair of the oxygen atom of the C-2 ether function and the nitrile molecule when they are positioned in a cis configuration. A 1,2-cis glycosyl oxazolinium intermediate is formed. This participation, in conjunction with the anomeric effect of the glycosyl donor, confers high 1,2-trans selectivities on glycosylations. Further application of this concept has led to efficient preparations of α-(1→5)-arabinan oligomers.
Multi-component one-pot synthesis of the tumor-associated carbohydrate antigen globo-H based on preactivation of thioglycosyl donors
Wang, Zhen,Zhou, Luyuan,El-Boubbou, Kheireddine,Ye, Xin-Shan,Huang, Xuefei
, p. 6409 - 6420 (2008/02/10)
(Chemical Equation Presented) Two efficient routes for the rapid assembly of the tumor-associated carbohydrate antigen Globo-H hexasaccharide 2 by a preactivation based iterative one-pot strategy are reported. The first method involves the sequential coup