793672-50-1Relevant academic research and scientific papers
A Concise Synthesis of Oligosaccharides Derived From Lipoarabinomannan (LAM) with Glycosyl Donors Having a Nonparticipating Group at C2
Li, Zhihao,Zheng, Changping,Terreni, Marco,Bavaro, Teodora,Sollogoub, Matthieu,Zhang, Yongmin
supporting information, p. 2033 - 2044 (2020/03/04)
Mycobacteria infection resulting in tuberculosis (TB) is one of the top ten leading causes of death over the world, and lipoarabinomannan (LAM) has been confirmed to play significant roles in this process. In this study, a convenient synthetic approach ha
In situ formation of β-glycosyl imidinium triflate from participating thioglycosyl donors: Elaboration to disarmed-armed iterative glycosylation
Lin, Yu Hsien,Ghosh, Bhaswati,Tony Mong, Kwok-Kong
supporting information, p. 10910 - 10912,3 (2020/09/16)
β-Glycosyl imidinium triflate is generated from participating thioglycoside donors for disarmed-armed iterative glycosylations and one-pot oligosaccharide synthesis.
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.
Iterative one-pot synthesis of oligosaccharides
Huang, Xuefei,Huang, Lijun,Wang, Haisheng,Ye, Xin-Shan
, p. 5221 - 5224 (2007/10/03)
Straight to the point! Preactivation of a p-tolyl thioglycoside donor, followed by sequential addition of p-tolyl thioglycosyl acceptors in one reaction flask allowed rapid syntheses of oligosaccharides independent of anomeric reactivities of donors and a
Stereospecific synthesis of 1,2-cis glycosides by vinyl-mediated IAD
Chayajarus, Kampanart,Chambers, David J.,Chughtai, Majid J.,Fairbanks, Antony J.
, p. 3797 - 3800 (2007/10/03)
(Chemical Equation Presented) Stereospecific 1,2-cis glycosylation of 2-O-vinyl thioglycosides, synthesized from the corresponding alcohols by Ir-catalyzed transvinylation with vinyl acetate, is achieved by iodine-mediated tethering of a range of primary
Allyl protecting group mediated intramolecular aglycon delivery: Optimisation of mixed acetal formation and mechanistic investigation
Cumpstey, Ian,Chayajarus, Kampanart,Fairbanks, Antony J.,Redgrave, Alison J.,Seward, Christopher M.P.
, p. 3207 - 3221 (2007/10/03)
An efficient protocol for the formation of α-iodo mixed acetals, the first step of allyl-mediated IAD, by reaction of allyl-derived enol ethers and alcohols, using I2, AgOTf and di-tert-butyl methylpyridine as a novel source of I+, i
