20672-66-6Relevant articles and documents
Tailoring chemoenzymatic oxidation: Via in situ peracids
Re, Rebecca N.,Proessdorf, Johanna C.,La Clair, James J.,Subileau, Maeva,Burkart, Michael D.
supporting information, p. 9418 - 9424 (2019/11/14)
Epoxidation chemistry often suffers from the challenging handling of peracids and thus requires in situ preparation. Here, we describe a two-phase enzymatic system that allows the effective generation of peracids and directly translate their activity to the epoxidation of olefins. We demonstrate the approach by application to lipid and olefin epoxidation as well as sulfide oxidation. These methods offer useful applications to synthetic modifications and scalable green processes.
Regio- and Stereoselective Synthesis of 1,2- cis-Glycosides by Anomeric O-Alkylation with Organoboron Catalysis
Izumi, Sanae,Kobayashi, Yusuke,Takemoto, Yoshiji
supporting information, p. 665 - 670 (2019/01/21)
Regio- and stereoselective synthesis of 1,2-cis-glycosides has been achieved by catalytic anomeric O-alkylation using organoboron compounds. Modulating steric and electronic factors of both catalysts and substrates enables activation of the axially oriented anomeric oxygens of glucose-derived dialkoxyborates. The mild reaction conditions allow broad functional-group tolerance. This approach can be applied to the efficient sequential synthesis of oligosaccharides.
Preparation method of tribenoside
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Paragraph 0028; 0029; 0030; 0034-0036; 0039-0040, (2018/04/02)
The invention discloses a preparation method of tribenoside. The method comprises the following steps: adding monoacetone glucose and a phase transfer catalyst to benzyl chloride, controlling the reaction temperature of a system, adding an inorganic base solution dropwise to obtain a crude product of tribenzyl monoacetone glucose, performing three-stage molecular distillation for purification toobtain high-purity tribenzyl monoacetone glucose, and adding high-purity tribenzyl monoacetone glucose to ethanol hydrochloride to prepare tribenoside. The method has the advantages of simple and efficient synthesis process, reasonable process, high synthesis efficiency and high yield; reaction operation is simple and convenient, tribenoside contains fewer impurities and is higher in purity and content, operation is convenient, and the European pharmacopoeia standards can be met directly.
Synthesis and binding affinity analysis of α1-2- and α1-6-O/S-linked dimannosides for the elucidation of sulfur in glycosidic bonds using quartz crystal microbalance sensors
Norberg, Oscar,Wu, Bin,Thota, Niranjan,Ge, Jian-Tao,Fauquet, Germain,Saur, Ann-Kathrin,Aastrup, Teodor,Dong, Hai,Yan, Mingdi,Ramstr?m, Olof
supporting information, p. 35 - 42 (2017/10/25)
The role of sulfur in glycosidic bonds has been evaluated using quartz crystal microbalance methodology. Synthetic routes towards α1-2- and α1-6-linked dimannosides with S- or O-glycosidic bonds have been developed, and the recognition properties assessed in competition binding assays with the cognate lectin concanavalin A. Mannose-presenting QCM sensors were produced using photoinitiated, nitrene-mediated immobilization methods, and the subsequent binding study was performed in an automated flow-through instrumentation, and correlated with data from isothermal titration calorimetry. The recorded Kd-values corresponded well with reported binding affinities for the O-linked dimannosides with affinities for the α1-2-linked dimannosides in the lower micromolar range. The S-linked analogs showed slightly disparate effects, where the α1-6-linked analog showed weaker affinity than the O-linked dimannoside, as well as positive apparent cooperativity, whereas the α1-2-analog displayed very similar binding compared to the O-linked structure.
Organo-zinc Promoted Diastereoselective C-Arylation of 1,2-Anhydrosugars from Arylboronic Acids
Tatina, Madhu Babu,Kusunuru, Anil Kumar,Mukherjee, Debaraj
, p. 4624 - 4627 (2015/09/28)
α-C-arylglycosides can be obtained through the addition of aryl zinc reagents to sugar epoxides. The required aryl zinc nucleophiles can be easily obtained from the corresponding boronic acids by B-Zn exchange and attack sugar 1,2 epoxides in a highly diastereoselective fashion to generate 1,2-cis-α-hexapyranosyl aryl glycosides under ligand- and base-free conditions.
A tin-free regioselective radical de-o-benzylation by an intramolecular hydrogen atom transfer on carbohydrate templates
Attouche, Angie,Urban, Dominique,Beau, Jean-Marie
, p. 9572 - 9575 (2013/09/23)
Radically selective: A remarkable 1,7-hydrogen atom transfer of a benzylic hydrogen atom to an O-silylmethylene radical initiates a regioselective de-O-benzylation of benzylated saccharides. The reaction terminates by an ionic mechanism and is general for hydroxy benzylated substrates having a variety of functional groups. Copyright
Armed-disarmed effect on the stability of cysteine thioglucosides
Nokwequ, Mbulelo G.,Nkambule, Comfort M.,Gammon, David W.
, p. 18 - 23 (2013/01/14)
Thioglucosides of cysteine show variable stability depending on the nature of the protecting groups on the glycosyl donor. Armed protecting groups (benzyl) lead to products that decompose readily while disarmed protecting groups (acetyl) lead to more stable products. Since this armed/disarmed effect of the protecting group on the stability of the thioglucosides is more pronounced for cysteine with an unprotected carboxylic group, the proposed mechanism is that decomposition is initiated by an intramolecular protonation of glycosyl sulfide and subsequent displacement of the sulfide by adventitious nucleophiles.
Stereoselective tandem epoxidation-alcoholysis/hydrolysis of glycals with molybdenum catalysts
Marin, Irene,Matheu, M. Isabel,Diaz, Yolanda,Castillon, Sergio
supporting information; experimental part, p. 3407 - 3418 (2011/02/23)
Molybdenum catalysts are efficient and selective catalysts for the tandem epoxidation/alcoholysis or epoxidation/hydrolysis of glucal and galactal derivatives. In glucal derivatives the selectivity is mainly controlled by the allylic substituent at position 3 of the glycal, obtaining in general the products derived from the initial formation of the α-epoxide (gluco) when this hydroxy group is protected, while products derived from the β-epoxide (manno) are mainly obtained when it is unprotected. In galactal derivatives the estereoselectivity is always high to give the α-epoxide (galacto) and independent of the protecting groups. Copyright
Synthesis of truncated analogues for studying the process of glycosyl phosphatidylinositol modification
John, Franklin,Hendrickson, Tamara L.
supporting information; experimental part, p. 2080 - 2083 (2010/07/03)
Figure presented Many eukaryotic proteins are modified with a glycosylphosphatidylinositol (GPI) anchor at their C-termini. This post-translational modification causes these proteins to be noncovalently tethered to the plasma membrane. The synthesis of tr
Sequential one-pot glycosidations catalytically promoted: Unprecedented strategy in oligosaccharide synthesis for the straightforward assemblage of the antitumor PI-88 pentasaccharide
Valerio, Silvia,Pastore, Antonello,Adinolfi, Matteo,Iadonisi, Alfonso
, p. 4496 - 4503 (2008/09/21)
(Chemical Equation Presented) The pentasaccharide sequence of the most active components of the antitumor drug PI-88, currently in phase II clinical trial, has been rapidly assembled in high overall yield and in only three steps starting from three monosa
