681831-82-3Relevant 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
, 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
A five-component one-pot synthesis of phosphatidylinositol pentamannoside (PIM5)
Wang, Dong,Xiong, De-Cai,Ye, Xin-Shan
, p. 1340 - 1342 (2018/01/08)
A practical and efficient synthesis of phosphatidylinositol pentamannoside (PIM5) was achieved based on a five-component one-pot sequential glycosylation protocol with exclusive regio- and stereo-selectivity. Two regioselective sequential glycosylations on inositol and p-tolyl thioglycosides as the sole type of building blocks made this protocol to avoid the tedious protective group manipulations. This synthetic strategy provides access to other important glycolipids with similar structures.
Synthesis of a tristearoyl lipomannan via preactivation-based iterative one-pot glycosylation
Gao, Jian,Guo, Zhongwu
, p. 12717 - 12725 (2014/01/17)
A convergent and efficient strategy was developed for the synthesis of lipomannan (LM), useful for vaccine development. Thioglycosides were employed as glycosyl donors to construct two key pseudotrisaccharide and tetramannose intermediates through preacti
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
, 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
, 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.
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
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
