95084-13-2Relevant academic research and scientific papers
A Mechanistic Probe into 1,2-cis Glycoside Formation Catalyzed by Phenanthroline and Further Expansion of Scope
Li, Jiayi,Nguyen, Hien M.
supporting information, p. 4054 - 4066 (2021/07/16)
Phenanthroline, a rigid and planar compound with two fused pyridine rings, has been used as a powerful ligand for metals and a binding agent for DNA/RNA. We discovered that phenanthroline could be used as a nucleophilic catalyst to efficiently access high
Oxidative activation of C-S bonds with an electropositive nitrogen promoter enables orthogonal glycosylation of alkyl over phenyl thioglycosides
Kitowski, Annabel,Jiménez-Moreno, Ester,Salvadó, Míriam,Mestre, Jordi,Castillón, Sergio,Jiménez-Osés, Gonzalo,Boutureira, Omar,Bernardes, Gon?alo J.L.
, p. 5490 - 5493 (2017/11/07)
A method for the selective activation of thioglycosides that uses the N+-thiophilic reagent Omesitylenesulfonylhydroxylamine (MSH) as a promoter is presented. The reaction proceeds via anomeric mesitylensulfonate intermediates, which could be isolated and fully characterized by placing a fluorine atom at the C2 position. In the presence of a soft Lewis acid, glycosylation reaction proceeds at ambient temperature with good yields. It is further demonstrated that it is possible to orthogonally activate S-ethyl in the presence of S-phenyl donors, enabling the design of sequential glycosylation strategies.
Stereoselective Glycosylation Reactions
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Paragraph 0085-0087, (2014/10/16)
Disclosed is a method for selective synthesis of 1,2-cis-α-linked glycosides which does not require the use of the specialized protecting group patterns normally employed to control diastereoselectivity. Thioglycoside acceptors can be used, permitting ite
Selective synthesis of 1,2- cis -α-glycosides without directing groups. Application to iterative oligosaccharide synthesis
Chu, An-Hsiang Adam,Nguyen, Son Hong,Sisel, Jordan A.,Minciunescu, Andrei,Bennett, Clay S.
supporting information, p. 2566 - 2569 (2013/06/27)
A method for the highly selective synthesis of 1,2-cis-α-linked glycosides that does not require the use of the specialized protecting group patterns normally employed to control diastereoselectivity is described. Thioglycoside acceptors can be used, permitting iterative oligosaccharide synthesis. The approach eliminates the need for lengthy syntheses of monosaccharides possessing highly specialized and unconventional protecting group patterns.
Synthesis of Methyl 5'-Thio-&α-isomaltoside via an Acyclic Monothioacetal and Its Behavior toward Glucoamylase
Hashimoto, Hironobu,Kawanishi, Masashi,Yuasa, Hideya
, p. 556 - 560 (2007/10/03)
Methyl 5'-thio-α-isomaltoside (1), which contains the ring-sulfur analogue of the nonreducing glucoside of isomaltose, was synthesized from gentiobiose through a novel ring opening-recyclization approach.The nonreducing glucoside of per-O-benzylated phen
An Efficient and Stereocontrolled Synthesis of the Nephritogenoside Core Structure
Sasaki, Makoto,Tachibana, Kazuo,Nakanishi, Hiroshi
, p. 6873 - 6876 (2007/10/02)
An efficient and stereocontrolled synthesis of the core trisaccharide 2 of nephritogenic glycopeptide, nephritogenoside 1 is described.Key to our synthetic strategy was β-selective glycosylation without neighboring group participation. Key words: nephrito
