40246-26-2Relevant academic research and scientific papers
Protecting carbohydrates with ethers, acetals and orthoesters under basic conditions
Liang, Yang,Pedersen, Christian M.
supporting information, p. 7598 - 7601 (2021/09/22)
Chlorinated ethyl and vinyl ethers are introduced at various positions of carbohydrates. Depending on the relative stereochemistry, vinylethers, acetals or orthoesters are formed under basic conditions. The products are stable, but are easily deprotected
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.
Ionic liquids as phase transfer catalysts: Enhancing the biphasic extractive epoxidation reaction for the selective synthesis of β-O-glycosides
Santiago, Cintia C.,Lafuente, Leticia,Bravo, Rodolfo,Díaz, Gisela,Ponzinibbio, Agustín
, p. 3739 - 3742 (2017/09/02)
Ionic liquids promoted the direct epoxidation of glycals acting as PTC. 1,2-anhydrosugars were prepared by the oxidation of glycals under biphasic conditions with dimethydioxirane generated in situ from oxone/acetone and amphiphilic IL's as catalysts. β-O
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
An efficient stereoselective dihydroxylation of glycals using a bimetallic system, RuCl3/CeCl3/NaIO4
Tiwari, Pallavi,Misra, Anup Kumar
, p. 2911 - 2913 (2007/10/03)
A catalytic dihydroxylation reaction on glycals has been developed using a bimetallic oxidizing system to furnish sugar 1,2-diols in a highly setroselective manner.
