cas 4291-69-4, 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GALACTOPYRANOSE

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Electrochemical Synthesis of Glycosyl Fluorides Using Sulfur(VI) Hexafluoride as the Fluorinating Agent
This manuscript describes the electrochemical synthesis of 17 different glycosyl fluorides in 73-98% yields on up to a 5 g scale that relies on the use of SF6 as an inexpensive and safe fluorinating agent. Cyclic voltammetry and related mechanistic studies carried out subsequently suggest that the active fluorinating species generated through the cathodic reduction of SF6 are transient under these reductive conditions and that the sulfur and fluoride byproducts are effectively scavenged by Zn(II) to generate benign salts.
Kim, Sungjin,Nagorny, Pavel
p. 2294 - 2298
(2022/04/07)

Synthesis of nature product kinsenoside analogues with anti-inflammatory activity
Kinsenoside is the major bioactive component from herbal medicine with a broad range of pharmacological functions. Goodyeroside A, an epimer of kinsenoside, remains less explored. In this report we chemically synthesized kinsenoside, goodyeroside A and their analogues with glycan variation, chirality inversion at chiral center(s), and bioisosteric replacement of lactone with lactam. Among these compounds, goodyeroside A and its mannosyl counterpart demonstrated superior anti-inflammatory efficacy. Furthermore, goodyeroside A was found to suppresses inflammatory through inhibiting NF-κB signal pathway, effectively. Structure-activity relationship is also explored for further development of more promising kinsenoside analogues as drug candidates.
Song, Wei,Sun, Yong,Xu, Lintao,Sun, Yajing,Li, Tianlu,Peng, Peng,Lou, Hongxiang
supporting information

(2020/12/02)

Synthesis and conformational analysis of vicinally branched trisaccharide β-d-Galf-(1 → 2)-[β-d-Galf-(1 → 3)-]-α-GalpfromCryptococcus neoformansgalactoxylomannan
The synthesis of a vicinally branched trisaccharide composed of twod-galactofuranoside residues attachedviaβ-(1 → 2)- and β-(1 → 3)-linkages to the α-d-galactopyranoside unit has been performed for the first time. The reported trisaccharide represents the galactoxylomannan moiety first described in 2017, which is the capsular polysaccharide of the opportunistic fungal pathogenCryptococcus neoformansresponsible for life-threatening infections in immunocompromised patients. The NMR-data reported here for the synthetic model trisaccharide are in good agreement with the previously assessed structure of galactoxylomannan and are useful for structural analysis of related polysaccharides. The target trisaccharide as well as the constituent disaccharides were analyzed by a combination of computational and NMR methods to demonstrate good convergence of the theoretical and experimental results. The results suggest that the furanoside ring conformation may strongly depend on the aglycon structure. The reported conformational tendencies are important for further analysis of carbohydrate-protein interaction, which is critical for the host response towardC. neoformansinfection.
Dorokhova, Vera S.,Gerbst, Alexey G.,Komarova, Bozhena S.,Previato, José O.,Previato, Lúcia Mendon?a,Dmitrenok, Andrey S.,Shashkov, Alexander S.,Krylov, Vadim B.,Nifantiev, Nikolay E.
p. 2923 - 2931
(2021/04/14)

Regioselective Anomeric O-Benzyl Deprotection in Carbohydrates
A highly regioselective hydrogenolysis of the anomeric benzyl group is reported. The reaction involves selective acetolysis of benzyl acetals of various mono- and di-saccharides using 10 % Pd/C under hydrogen atmosphere in the presence of Na2CO
Anjaneyulu, Bandi,Rao, Boddu Umamaheswara,Sridhar, Perali Ramu
supporting information
p. 5665 - 5668
(2021/11/11)

Synthesis method of voglibose
The invention provides a synthesis method of voglibose, and solves the technical problems that in an existing synthesis method of voglibose, raw materials are difficult to obtain, high in price, large in investment, low in yield and not suitable for industrial production. The synthesis method comprises the steps: synthesizing a compound V by taking glucose monohydrate and sodium acetate as raw materials through eleven reaction steps; and preparing a compound VIII from the compound V through an addition reaction, a ring-opening reaction and an aldol condensation reaction, and thus obtaining voglibose through amination reduction of the compound VIII. The synthesis method of voglibose can be widely applied to the technical field of voglibose synthesis methods.
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(2021/08/07)

Method for continuously synthesizing benzyl-substituted glucolactone by adopting microchannel reaction device
The invention discloses a method for continuously synthesizing benzyl-substituted glucolactone by adopting a microchannel reaction device. The method comprises the following steps: taking methyl-alpha-D-mannopyranoside as an initial raw material, preparing the methyl-alpha-D-mannopyranoside into an old organic solvent solution, and reacting the old organic solvent solution with an organic solvent solution of benzyl chloride in a first microreactor to generate methyl glucose with hydroxyl protected by benzyl; reacting a homogeneous solution formed by mixing a reaction solution of benzyl-substituted gluconic acid and a small amount of hydrochloric acid solution in a second microreactor for demethylation to generate hydroxyl benzyl-substituted glucose; and finally, reacting the reaction solution with an aqueous solution of hydrogen peroxide and sodium hydroxide and an organic solvent solution of tetramethylpiperidine nitrogen oxide in a third microreactor to generate the high-purity hypoglycemic drug Dapagliflozin intermediate benzyl substituted glucolactone. The method disclosed by the invention is higher in heat and mass transfer efficiency and easier to industrially amplify, the initial materials are simple, cheap and easily available, the process is simple, the obtained intermediate is high in purity and high in yield, the production cost can be effectively reduced, and the method is suitable for industrial production.
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Paragraph 0012; 0043; 0045; 0047; 0050; 0052-0053; 0055

(2021/06/21)

Beta-D-glucose short-chain fatty acid ester compound as well as preparation method and application thereof
The invention discloses a beta-D-glucose short-chain fatty acid ester compound as well as a preparation method and application thereof, and belongs to the technical field of organic synthesis. The compound is a compound shown as a formula I, or a stereoisomer, a pharmaceutically acceptable salt, a solvate or a prodrug of the compound shown as the formula I. The formula is as shown in the description, wherein R is a methyl group, an ethyl group, a propyl group, a propylene group, an isopropylidene group, a butyl group, a butylidene group, an isobutylidene group, an amyl group, a pentylidene group or an isoamylidene group. The compound has potential prevention and treatment effects on diabetes, hyperlipidemia, atherosclerosis, Alzheimer's disease, cardiovascular and cerebrovascular diseases,inflammation, tumors and depression.
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Paragraph 0033; 0057; 0062

(2021/04/03)

Tuning the activity of iminosugars: novel N-alkylated deoxynojirimycin derivatives as strong BuChE inhibitors
We have designed unprecedented cholinesterase inhibitors based on 1-deoxynojirimycin as potential anti-Alzheimer’s agents. Compounds are comprised of three key structural motifs: the iminosugar, for interaction with cholinesterase catalytic anionic site (
Ahuja-Casarín, Ana I.,Merino-Montiel, Penélope,Vega-Baez, José Luis,Montiel-Smith, Sara,Fernandes, Miguel X.,Lagunes, Irene,Maya, Inés,Padrón, José M.,López, óscar,Fernández-Bola?os, José G.
p. 138 - 146
(2020/11/27)

Discovery of Salidroside-Derivated Glycoside Analogues as Novel Angiogenesis Agents to Treat Diabetic Hind Limb Ischemia
Therapeutic angiogenesis is a potential therapeutic strategy for hind limb ischemia (HLI); however, currently, there are no small-molecule drugs capable of inducing it at the clinical level. Activating the hypoxia-inducible factor-1 (HIF-1) pathway in skeletal muscle induces the secretion of angiogenic factors and thus is an attractive therapeutic angiogenesis strategy. Using salidroside, a natural glycosidic compound as a lead, we performed a structure-activity relationship (SAR) study for developing a more effective and druggable angiogenesis agent. We found a novel glycoside scaffold compound (C-30) with better efficacy than salidroside in enhancing the accumulation of the HIF-1α protein and stimulating the paracrine functions of skeletal muscle cells. This in turn significantly increased the angiogenic potential of vascular endothelial and smooth muscle cells and, subsequently, induced the formation of mature, functional blood vessels in diabetic and nondiabetic HLI mice. Together, this study offers a novel, promising small-molecule-based therapeutic strategy for treating HLI.
Han, Jingxuan,He, Yun,Huang, Song,Kasim, Vivi,Liu, Caiping,Marcelina, Olivia,Miyagishi, Makoto,Nugrahaningrum, Dyah Ari,Wang, Guixue,Wu, Shourong,Zou, Meijuan
supporting information

(2022/01/14)

Design, synthesis, and biological evaluation of desmuramyl dipeptides modified by adamantyl-1,2,3-triazole
Muramyl dipeptide (MDP) is the smallest peptidoglycan fragment able to trigger the immune response. Structural modification of MDP can lead to the preparation of analogs with improved immunostimulant properties, including desmuramyl peptides (DMPs). The aim of this work was to prepare the desmuramyl peptide (L-Ala-D-Glu)-containing adamantyl-triazole moiety and its mannosylated derivative in order to study their immunomodulatory activities in vivo. The adjuvant activity of the prepared compounds was evaluated in a murine model using ovalbumin as an antigen, and compared to the reference adjuvant ManAdDMP. The results showed that the introduction of the lipophilic adamantyl-triazole moiety at the C-terminus of L-Ala-D-Glu contributes to the immunostimulant activity of DMP, and that mannosylation of DMP modified with adamantyl-triazole causes the amplification of its immunostimulant activity.
?kalamera, Dani,Antica, Mariastefania,Car, ?eljka,Dra?enovi?, Josip,Milkovi?, Lidija,Perokovi?, Vesna Petrovi?,Ribi?, Rosana,Stojkovi?, Ranko,Tomi?, Sr?anka
(2021/11/01)

Self-Promoted Glycosylation for the Synthesis of β-N-Glycosyl Sulfonyl Amides
N-Glycosyl N-sulfonyl amides have been synthesized by a self-promoted glycosylation, i. e. without any catalysts, promotors or additives. When the reactions were carried out at lower temperatures a mixture of N- and O-glycosides were observed, where the latter rearranged to give the β-N-glycosides at elevated temperatures. By this method sulfonylated asparagine derivatives can be selectively β-glycosylated in high yields by trichloroacetimidate glycosyl donors of different reactivity including protected glucosamine derivatives. The chemoselectivity in the glycosylations as well as the rearrangements from O-glycosides to β-N-glycosides gives information of the glycosylation mechanism. This method gives access to glycosyl sulfonyl amides under mild conditions.
Ma?a, Patrycja,Pedersen, Christian Marcus
p. 5685 - 5689
(2021/08/30)

Synthesis of photolabile group protected anomeric acetals and its application in carbohydrate synthesis with the assistance of continuous flow photo-reactor
Selective deprotection of photolabile anomeric 2-nitrobenzyl acetals was achieved using continuous flow photo-reactor (UV radiation at 355 nm) in methanol-water. Various protecting groups such as acetyl, benzyl, benzoyl, benzylidine, TBS, etc. were found to be highly stable during the photolysis.
Tiwari, Varsha,Badavath, Vishnu Nayak,Singh, Adesh Kumar,Kandasamy, Jeyakumar
p. 227 - 236
(2020/03/18)

Pivaloyl-protected glucosyl iodide as a glucosyl donor for the preparation of β-C-glucosides
A method for the selective synthesis of β-C-glucosides using α-D-tetra-O-pivaloylglucosyl iodide as a glucosyl donor is reported. Its diastereoselectivity differs from that of the respective acetyl-protected glucosyl bromide, as it reported in the literature under similar reaction conditions. The concentration of the catalyst, the solvent and the type of additive used are crucial factors that determine the reaction selectivity. This method has been applied in a short synthesis of dapagliflozin. The stability of α-D-tetra-O-pivaloylglucosyl iodide in CDCl3 and THF at reflux was also studied. All side products in the coupling and decomposition reactions were isolated and characterized, and possible pathways for their formation are proposed.
Triantakonstanti, Virginia V.,Toskas, Alexandros,Iordanidis, Nicolaos S.,Andreou, Thanos,Koftis, Theoharis V.,Gallos, John K.
supporting information

(2020/07/13)

Glucosylpolyphenols as Inhibitors of Aβ-Induced Fyn Kinase Activation and Tau Phosphorylation: Synthesis, Membrane Permeability, and Exploratory Target Assessment within the Scope of Type 2 Diabetes and Alzheimer's Disease
Despite the rapidly increasing number of patients suffering from type 2 diabetes, Alzheimer's disease, and diabetes-induced dementia, there are no disease-modifying therapies that are able to prevent or block disease progress. In this work, we investigate the potential of nature-inspired glucosylpolyphenols against relevant targets, including islet amyloid polypeptide, glucosidases, and cholinesterases. Moreover, with the premise of Fyn kinase as a paradigm-shifting target in Alzheimer's drug discovery, we explore glucosylpolyphenols as blockers of Aβ-induced Fyn kinase activation while looking into downstream effects leading to Tau hyperphosphorylation. Several compounds inhibit Aβ-induced Fyn kinase activation and decrease pTau levels at 10 μM concentration, particularly the per-O-methylated glucosylacetophloroglucinol and the 4-glucosylcatechol dibenzoate, the latter inhibiting also butyrylcholinesterase and β-glucosidase. Both compounds are nontoxic with ideal pharmacokinetic properties for further development. This work ultimately highlights the multitarget nature, fine structural tuning capacity, and valuable therapeutic significance of glucosylpolyphenols in the context of these metabolic and neurodegenerative disorders.
De Matos, Ana M.,Blázquez-Sánchez, M. Teresa,Bento-Oliveira, Andreia,De Almeida, Rodrigo F. M.,Nunes, Rafael,Lopes, Pedro E. M.,MacHuqueiro, Miguel,Cristóv?o, Joana S.,Gomes, Cláudio M.,Souza, Cleide S.,El Idrissi, Imane G.,Colabufo, Nicola A.,Diniz, Ana,Marcelo, Filipa,Oliveira, M. Concei??o,López, óscar,Fernandez-Bola?os, José G.,D?twyler, Philipp,Ernst, Beat,Ning, Ke,Garwood, Claire,Chen, Beining,Rauter, Amélia P.
p. 11663 - 11690
(2020/11/26)

Photo-induced glycosylation using a diaryldisulfide as an organo-Lewis photoacid catalyst
Photo-induced glycosylations of several acceptors with trichloroacetimidate donors using bis(2-naphthyl)disulfide as an organo-Lewis photoacid (LPA) catalyst proceeded effectively to give the corresponding glycosides in good to high yields. In addition, t
Iibuchi, Naoto,Eto, Takahiro,Aoyagi, Manabu,Kurinami, Reiji,Sakai, Hayato,Hasobe, Taku,Takahashi, Daisuke,Toshima, Kazunobu
supporting information
p. 851 - 855
(2020/02/15)

STABLE VACCINE AGAINST CLOSTRIDIUM DIFFICILE
The present invention relates to a synthetic saccharide of general formula (I) that is related to Clostridium difficile PS-II cell-surface polysaccharide and conjugate thereof. Said synthetic saccharide, said conjugate and pharmaceutical composition containing said synthetic saccharide or said conjugate are useful for prevention and/or treatment of diseases associated with Clostridium difficile. Furthermore, the synthetic saccharide of general formula (I) is useful as marker in immunological assays for detection of antibodies against Clostridium difficile bacteria.
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Page/Page column 134; 165

(2020/06/10)

Aza-carboside chalcone and preparation method thereof (by machine translation)
The aza-carboside chalcone comprises a compound, wherein the compound of the general formula I or the general formula II is compatible with industrial production, has small toxic and side effects, has a rapid hypoglycemic effect, and can better relieve symptoms; namely, a diabetic patient . the invention provides a preparation method of the azinosine chalcone, which comprises a compound of general formula I or general formula II and an inorganic acid or an organic acid. (by machine translation)
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Paragraph 0089; 0094-0095

(2019/07/31)

Establishment of Guidelines for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity
Stereocontrolled chemical glycosylation remains a major challenge despite vast efforts reported over many decades and so far still mainly relies on trial and error. Now it is shown that the relative reactivity value (RRV) of thioglycosides is an indicator for revealing stereoselectivities according to four types of acceptors. Mechanistic studies show that the reaction is dominated by two distinct intermediates: glycosyl triflates and glycosyl halides from N-halosuccinimide (NXS)/TfOH. The formation of glycosyl halide is highly correlated with the production of α-glycoside. These findings enable glycosylation reactions to be foreseen by using RRVs as an α/β-selectivity indicator and guidelines and rules to be developed for stereocontrolled glycosylation.
Chang, Chun-Wei,Wu, Chia-Hui,Lin, Mei-Huei,Liao, Pin-Hsuan,Chang, Chun-Chi,Chuang, Hsiao-Han,Lin, Su-Ching,Lam, Sarah,Verma, Ved Prakash,Hsu, Chao-Ping,Wang, Cheng-Chung
p. 16775 - 16779
(2019/11/03)

Matching Glycosyl Donor Reactivity to Sulfonate Leaving Group Ability Permits SN2 Glycosylations
Here we demonstrate that highly β-selective glycosylation reactions can be achieved when the electronics of a sulfonyl chloride activator and the reactivity of a glycosyl donor hemiacetal are matched. While these reactions are compatible with the acid- and base-sensitive protecting groups that are commonly used in oligosaccharide synthesis, these protecting groups are not relied upon to control selectivity. Instead, β-selectivity arises from the stereoinversion of an α-glycosyl arylsulfonate in an SN2-like mechanism. Our mechanistic proposal is supported by NMR studies, kinetic isotope effect (KIE) measurements, and DFT calculations.
Zhuo, Ming-Hua,Wilbur, David J.,Kwan, Eugene E.,Bennett, Clay S.
supporting information
p. 16743 - 16754
(2019/10/16)

Introducing Oxo-Phenylacetyl (OPAc) as a Protecting Group for Carbohydrates
A series of oxo-phenylacetyl (OPAc)-protected saccharides, with divergent base sensitivity profiles against benzoyl (Bz) and acetyl (Ac) were synthesized, and KHSO5/AcCl in methanol was identified as an easy, mild, selective, and efficient deprotecting reagent for their removal in the perspective of carbohydrate synthesis. Timely monitoring of AcCl reagent was supportive in both sequential and simultaneous deprotecting of OPAc, Bz, and Ac. The salient feature of our method is the orthogonal stability against different groups, its ease to generate different valuable acceptors using designed monosaccharides, and use of OPAc as a glycosyl donar.
Kumar, Atul,Gannedi, Veeranjaneyulu,Rather, Suhail A.,Vishwakarma, Ram A.,Ahmed, Qazi Naveed
p. 4131 - 4138
(2019/04/30)

Synthesis of Phenolic Glycosides: Glycosylation of Sugar Lactols with Aryl Bromides via Dual Photoredox/Ni Catalysis
Multifarious sugar lactols were efficiently transformed into the corresponding phenolic glycosides by treating with aryl bromides in acetonitrile with Ir[dF(CF3)ppy]2(dtbbpy)(PF6) as a photocatalyst under visible light irr
Ye, Hui,Xiao, Cong,Zhou, Quan-Quan,Wang, Peng George,Xiao, Wen-Jing
supporting information
p. 13325 - 13334
(2018/11/02)

Method for synthesizing 2,3,4,6-tetrabenzyl-D-glucopyranose
The invention discloses a method for synthesizing 2,3,4,6-tetrabenzyl-D-glucopyranose. The method is characterized by comprising the following steps: a, dissolving alpha-D-methylglucoside into an organic solvent, introducing nitrogen, adding metal hydride
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Paragraph 0035; 0037; 0038; 0040; 0041; 0043; 0044; 0046

(2018/04/26)

Formation of and Glycosylation with Per-O-Acetyl Septanosyl Halides: Rationalizing Complex Reactivity En Route to p-Nitrophenyl Septanosides
Protein–carbohydrate interactions are at the heart of many biological processes. For lectins, those interactions result simply in the association of two species, whereas for enzymes like glycosidases, association ultimately leads to cleavage and formation
Pote, Aditya R.,Vannam, Raghu,Richard, Alissa,Gascón, José,Peczuh, Mark W.
supporting information
p. 1709 - 1719
(2018/04/24)

An Empirical Understanding of the Glycosylation Reaction
Reliable glycosylation reactions that allow for the stereo- and regioselective installation of glycosidic linkages are paramount to the chemical synthesis of glycan chains. The stereoselectivity of glycosylations is exceedingly difficult to control due to the reaction's high degree of sensitivity and its shifting, simultaneous mechanistic pathways that are controlled by variables of unknown degree of influence, dominance, or interdependency. An automated platform was devised to quickly, reproducibly, and systematically screen glycosylations and thereby address this fundamental problem. Thirteen variables were investigated in as isolated a manner as possible, to identify and quantify inherent preferences of electrophilic glycosylating agents (glycosyl donors) and nucleophiles (glycosyl acceptors). Ways to enhance, suppress, or even override these preferences using judicious environmental conditions were discovered. Glycosylations involving two specific partners can be tuned to produce either 11:1 selectivity of one stereoisomer or 9:1 of the other by merely changing the reaction conditions.
Chatterjee, Sourav,Moon, Sooyeon,Hentschel, Felix,Gilmore, Kerry,Seeberger, Peter H.
supporting information
p. 11942 - 11953
(2018/09/27)

REAGENTS AND METHODS FOR GLYCOSYLATION
The invention provides methods and regents for the glycosylation of organic molecules. In one aspect, the invention provides a method for glycosylating a hydroxyl-containing organic compound (i.e., a glycosyl acceptor) comprising contacting a glycosyl don
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Paragraph 00173

(2018/03/09)

The tertiary-butyl group: Selective protection of the anomeric centre and evaluation of its orthogonal cleavage
The tertiary-butyl group has not been examined extensively as a protecting group. In this work, we describe the synthesis of tert-butyl glycosides via the Fischer glycosylation protocol. Furthermore, its utility as a temporary anomeric protecting group was evaluated. A range of differentially protected monosaccharides was used to investigate the stability of the tert-butyl group upon the introduction of other protecting groups; and compatibility of its cleavage in the presence of the latter.
Subratti, Afraz,Jalsa, Nigel Kevin
supporting information
p. 2082 - 2085
(2018/05/04)

Enhanced Spacer Length between Mannose Mimicking Shikimoyl and Quinoyl Headgroups and Hydrophobic Region of Cationic Amphiphile Increases Efficiency of Dendritic Cell Based DNA Vaccination: A Structure-Activity Investigation
In the field of dendritic cell based genetic immunization, previously we showed that liposomes of cationic amphiphiles containing mannose-mimicking shikimoyl headgroup are promising DNA vaccine carriers for dendritic cell (DC) transfection. The present structure-activity study reports on the influence of spacer length (between mannose-mimicking headgroups and quaternary nitrogen centers) in modulating the DC-transfection efficiencies. Further, we report on the anti-melanoma immune response inducing properties of the promising cationic amphiphiles in syngeneic C57BL/6J mice under prophylactic settings.
Voshavar, Chandrashekhar,Meka, Rakesh C. R.,Samanta, Sanjoy,Marepally, Srujan,Chaudhuri, Arabinda
p. 1605 - 1610
(2017/03/08)

A 1,2-trans-Selective Glycosyl Donor Bearing Cyclic Protection at the C-2 and C-3 Hydroxy Groups
A new 1,2-trans-selective glycosylation reaction is described. Glucosyl donors protected cyclically at the C-2 and C-3 hydroxy groups as six- (butane diacetal), seven- (tetraisopropyldisiloxanylidene), or eight- (2,3-o-xylylene) membered fused rings were synthesized in a straightforward manner. The glycosylation reactions of the glucosyl donors with various acceptors mainly generated β-glycosides under conventional reaction conditions. The results show that the o-xylylene group is a suitable 1,2-trans-directing group from the points of view of stereoselectivity and chemical stability. A conformational study of the oxocarbenium ion of an o-xylylene-protected glucose derivative by NMR spectroscopy and computational simulation was carried out. The results imply that the oxocarbenium ion mainly adopts a 4H3 conformation owing to the rigid trans-fused ring at C-2 and C-3, while a noncyclically protected derivative might fluctuate between conformations. These results suggest that an eclipsing interaction between the pseudoequatorial xyloxy group at C-2 and the incoming nucleophile hampers 1,2-cis attack.
Yagami, Nahoko,Tamai, Hideki,Udagawa, Taro,Ueki, Akiharu,Konishi, Miku,Imamura, Akihiro,Ishida, Hideharu,Kiso, Makoto,Ando, Hiromune
supporting information
p. 4778 - 4785
(2017/09/07)

Oxidative activation of C-S bonds with an electropositive nitrogen promoter enables orthogonal glycosylation of alkyl over phenyl thioglycosides
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.
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)

Sugar hydrazide imides: A new family of glycosidase inhibitors
The preparation of a novel type of iminosugar including a hydrazide imide moiety is described. The sugar hydrazide imides (3S,4S,5R,6R)-1-amino-3,4,5-trihydroxy-6-(hydroxymethyl)-2-iminopiperidine acetate and (3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethy
Lindb?ck, Emil,Lopéz, óscar,Tobiesen, ?dne,Fernández-Bola?os, José G.,Sydnes, Magne O.
supporting information
p. 8709 - 8712
(2017/11/03)

Synthesis of Mannosylglycerate Derivatives as Immunostimulating Agents
Mannosylglycerate (MG) is a compatible solute extracted from some red algae and bacteria. Thanks to its ability to protect proteins and stabilise enzymes, MG has been widely studied for its uses against neurodegenerative diseases, and also in biotechnology. More recently, its immunostimulating properties against chronic lymphocytic leukaemia have been investigated. In this paper, we report the synthesis of MG derivatives, and a preliminary biological study on their capacity to behave as immunostimulating agents. We investigated their toxicity against peripheral blood mononuclear cells from healthy donors and their ability to increase the phagocytosis of opsonised bacteria by polynuclear neutrophils. This resulted in the discovery of two new molecules as potential immunostimulating agents.
Hamon, Nadège,Mouline, Caroline C.,Travert, Marion
p. 4803 - 4819
(2017/09/07)

Total synthesis of mangiferin, homomangiferin, and neomangiferin
Total synthesis of mangiferin, homomangiferin, and neomangiferin, three C-glycosyl xanthone natural products with a wide spectrum of pharmacological effects, has been achieved starting from 2,3,4,6-tetra-O-benzyl-α/β-d-glucopyranose. The key steps involve a stereoselective Lewis acid promoted C-glycosylation of protected phloroglucinol with tetrabenzylglucopyranosyl acetate and a highly regioselective base-induced cyclization for the construction of the core xanthone skeleton.
Wei, Xiong,Liang, Danlin,Wang, Qing,Meng, Xiangbao,Li, Zhongjun
p. 8821 - 8831
(2016/10/03)

Four of a kind of preparation method of hexose phenmethyl pyranoid form
The invention provides a method for preparing tetrabenzyl pyran type hexose, belonging to the field of sugar compounds. The method adopts a supported solid-acid catalyst namely silica gel supported sulfuric acid-hydrofluoric acid, performs catalytic hydro
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Paragraph 0050-0053

(2017/06/21)

Synthesis of Unprecedented Sulfonylated Phosphono-exo-Glycals Designed as Inhibitors of the Three Mycobacterial Galactofuranose Processing Enzymes
This study reports a new methodology to synthesize exo-glycals bearing both a sulfone and a phosphonate. This synthetic strategy provides a way to generate exo-glycals displaying two electron-withdrawing groups and was applied to eight different carbohydrates from the furanose and pyranose series. The Z/E configurations of these tetrasubstituted enol ethers could be ascertained using NMR spectroscopic techniques. Deprotection of an exo-glycal followed by an UMP (uridine monophosphate) coupling generated two new UDP (uridine diphosphate)-galactofuranose analogues. These two Z/E isomers were evaluated as inhibitors of UGM, GlfT1, and GlfT2, the three mycobacterial galactofuranose processing enzymes. Molecule 46-(E) is the first characterized inhibitor of GlfT1 reported to date and was also found to efficiently inhibit UGM in a reversible manner. Interestingly, GlfT2 showed a better affinity for the (Z) isomer. The three enzymes studied in the present work are not only interesting because, mechanistically, they are still the topic of intense investigations, but also because they constitute very important targets for the development of novel antimycobacterial agents.
Frédéric, Christophe J.-M.,Tikad, Abdellatif,Fu, Jian,Pan, Weidong,Zheng, Ruixiang B.,Koizumi, Akihiko,Xue, Xiaochao,Lowary, Todd L.,Vincent, Stéphane P.
supporting information
p. 15913 - 15920
(2016/10/25)

Total synthesis of N-butyl-1-deoxynojirimycin
N-Butyl-1-deoxynojirimycin (NB-DNJ) derived from imino sugar deoxynojirimycin (DNJ) has been approved for the treatment of Gaucher’s disease. Herein, a facile and efficient synthetic procedure for NB-DNJ has been described. Comparing to the methods reported previously,methanesulfonyl group was used as a leaving group for easy displacement upon attack by the imine in the sugar ring, leading to a high yield during the introduction of the n-butyl group. Thismethod can serve as an excellent protocol for the synthesis of DNJ derivatives with a variety of N-alkyl substituents and for large-scale production.
Wang, Jiajia,Zhao, Yunyan,Zhao, Wei,Wang, Peng,Li, Jing
p. 445 - 454
(2017/08/23)

Selenoureido-iminosugars: A new family of multitarget drugs
Herein we report the synthesis of N-alkylated deoxynojirimycin derivatives decorated with a selenoureido motif at the hydrocarbon tether as an example of unprecedented multitarget agents. Title compounds were designed as dual drugs for tackling simultaneously the Gaucher disease (by selective inhibition of β-glucosidase, Ki= 1.6–5.5 μM, with improved potency and selectivity compared to deoxynojirimycin) and its neurological complications (by inhibiting AChE, Kiup to 5.8 μM). Moreover, an excellent mimicry of the selenoenzyme glutathione peroxidase was also found for the catalytic scavenging of H2O2(Kcat/Kuncatup to 640) using PhSH as a cofactor, with improved activity compared to known positive controls, like (PhSe)2and ebselen; therefore, such compounds are also excellent scavengers of peroxides, an example of reactive oxygen species present at high concentrations in patients of Gaucher disease and neurological disorders.
Olsen, Jacob Ingemar,Plata, Gabriela B.,Padrón, José M.,López, óscar,Bols, Mikael,Fernández-Bola?os, José G.
p. 155 - 160
(2016/08/01)

Total Synthesis of (+)-Vicenin-2
The bis-C-glucosyl flavonoid vicenin-2 (1) has been synthesized by exploiting bis-C-glycosylation of 1,3,5-trifluorobenzene and aromatic nucleophilic substitution to transform fluorine atoms to oxygen functions in excellent yield.
Ho, Thanh C.,Kamimura, Haruki,Ohmori, Ken,Suzuki, Keisuke
supporting information
p. 4488 - 4490
(2016/09/28)

Stereocontrolled Photoinduced Glycosylation Using an Aryl Thiourea as an Organo photoacid
Photoinduced glycosylation of alcohols with α-glucosyl trichloroacetimidates, using aryl urea and thioureas as organo photoacids, was examined under long wavelength UV (ultraviolet) irradiation. The results show, for the first time, that such glycosylatio
Kimura, Tomoya,Eto, Takahiro,Takahashi, Daisuke,Toshima, Kazunobu
supporting information
p. 3190 - 3193
(2016/07/14)

A versatile glycosylation strategy: Via Au(III) catalyzed activation of thioglycoside donors
Among various methods of chemical glycosylations, glycosylation by activation of thioglycoside donors using a thiophilic promoter is an important strategy. Many promoters have been developed for the activation of thioglycosides. However, incompatibility w
Vibhute, Amol M.,Dhaka, Arun,Athiyarath, Vignesh,Sureshan, Kana M.
p. 4259 - 4263
(2016/07/06)

SGLT-2 INHIBITORS
Provided are compounds of SGLT-2 inhibitors, pharmaceutically acceptable salts, hydrides and stereoisomers thereof. The compounds are employed in pharmaceutical compositions, and methods of making and use, including treating a person in need thereof with
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(2016/04/09)

Gold-catalysed glycosylation reaction using an easily accessible leaving group
Gold(iii)-catalysed glycosylation reaction has been developed by employing a new and easily accessible leaving group synthesized from ethyl cyanoacetate. Several nucleophiles like alcohols, thiols, allyltrimethylsilane, trimethylsilyl azide and triethylsilane have been reacted to make the corresponding glycosides in good yields and with marginal to excellent α-selectivity. This journal is
Koppolu, Srinivasa Rao,Niddana, Ramana,Balamurugan, Rengarajan
p. 5094 - 5097
(2015/05/13)

Iodine monochloride (ICl) as a highly efficient, green oxidant for the oxidation of alcohols to corresponding carbonyl compounds
Iodine monochloride (ICl) was discovered to be a highly efficient, green oxidant, which can oxidize aldose hemiacetals, diarylmethanols, arylalkylmethanols, anddialkylmethanols to the corresponding aldose lactones, diarylmethanones, arylalkylmethanones, and dialkylmethanones, respectively, in high yields. ICl as a green, metal-free oxidant is characterized by mild reaction condition, short reaction time, good yield, and broad scope.
Wei, Peng,Zhang, Datong,Gao, Zhigang,Cai, Wenqing,Xu, Weiren,Tang, Lida,Zhao, Guilong
supporting information
p. 1457 - 1470
(2015/05/20)

NEW C-GLYCOSYLPOLYPHENOL ANTIDIABETIC AGENTS, EFFECT ON GLUCOSE TOLERANCE AND INTERACTION WITH BETA-AMYLOID. THERAPEUTIC APPLICATIONS OF THE SYNTHESIZED AGENT(S) AND OF GENISTA TENERA ETHYL ACETATE EXTRACTS CONTAINING SOME OF THOSE AGENTS
The present invention concerns the antidiabetic-activity of compounds type A, namely of 8-β-D-glucosylgenistein, which is not toxic to eukaryotic cells and has demonstrated to produce complete normalization of fasting hyperglycaemia, to reduce excessive p
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Paragraph 0077; 0085; 0086

(2015/02/19)

SrCl2 as an efficient cocatalyst for acidic hydrolysis of methyl glycosides
SrCl2 was found to be the most efficient cocatalyst for the acidic hydrolysis of methyl glycosides after 26 kinds of most representative metal salts were screened. The SrCl2-cocatalyzed acidic hydrolysis of methyl glycosides is highl
Shi, Yong-Heng,Xie, Ya-Fei,Liu, Yu-Qiang,Wei, Qun-Chao,Xu, Wei-Ren,Tang, Li-Da,Zhao, Gui-Long
p. 561 - 566
(2014/05/06)

Carbohydrate-derived iminium salt organocatalysts for the asymmetric epoxidation of alkenes
A new family of carbohydrate-based dihydroisoquinolinium salts has been prepared and tested for potential as asymmetric catalysts for the epoxidation of unfunctionalized alkene substrates, providing up to 57% ee in the product epoxides.
Bulman Page, Philip C.,Chan, Yohan,Liddle, John,Elsegood, Mark R.J.
p. 7283 - 7305
(2017/09/13)

CARBOHYDRATE PHOSPHONATE DERIVATIVES AS MODULATORS OF GLYCOSYLATION
Compounds of Formula (I) are useful as modulators of glycosylation. Compounds of Formula (I) have the following structure: (I) and the definitions of the other variables are provided herein.
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Paragraph 0121

(2014/09/03)

Exploiting the therapeutic potential of 8-β- d -glucopyranosylgenistein: Synthesis, antidiabetic activity, and molecular interaction with islet amyloid polypeptide and amyloid β-peptide (1-42)
8-β-d-Glucopyranosylgenistein (1), the major component of Genista tenera, was synthesized and showed an extensive therapeutical impact in the treatment of STZ-induced diabetic rats, producing normalization of fasting hyperglycemia and amelioration of exce
Jesus, Ana R.,Dias, Catarina,Matos, Ana M.,De Almeida, Rodrigo F.M.,Viana, Ana S.,Marcelo, Filipa,Ribeiro, Rogério T.,Macedo, Maria P.,Airoldi, Cristina,Nicotra, Francesco,Martins, Alice,Cabrita, Eurico J.,Jiménez-Barbero, Jesús,Rauter, Amélia P.
p. 9463 - 9472
(2015/02/02)

GEM-DIFLUORINATED C-GLYCOSIDE COMPOUNDS AS ANTI-CANCER AGENTS
The present document describes a synthesis of a class of gem-difluorinated C-glycoside compounds derived from podophyllotoxin, which may be used, but not exclusively, in oncology for the treatment of cancer. More particularly, the podophyllotoxin gem-difluorinated C-glycoconjugated derivatives display improved conformational and chemical stability, and improved cytotoxicity exhibited against drug-resistant cancer cell lines.
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Paragraph 00128; 00129; 00130

(2014/07/23)

NKT CELL LIGANDS AND METHODS OF USE
Alpha-glycosylceramide compounds capable of activating NKT cells and compositions thereof are disclosed. Methods for activating NKT cells, methods of stimulating an immune response in a subject, and methods of treating cancer, infectious diseases, autoimmune diseases and disorders, or allergy diseases or disorders with the compounds and compositions are also disclosed.
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Sheet 1

(2015/01/16)

Synthesis of C-spiro-glycoconjugates from sugar lactones via zinc mediated Barbier reaction
Anomeric gem-diallylation, mono-β-crotylation and mono-β- propargylation of sugar 1,5 and 1,4 lactones have been achieved under Barbier reaction conditions using Zn powder and a catalytic amount of TMSCl as an activator. Ring closing olefin metathesis of the synthesized gem-diallyl derivatives furnished C-spiro cyclopentene glycosides. Finally, the cyclopentene rings were converted into carbohydrate based tricyclic morpholine fused triazole glycoconjugates as potential SGLT2 inhibitors.
Lambu, Mallikharjuna Rao,Hussain, Altaf,Sharma, Deepak K.,Yousuf, Syed Khalid,Singh, Baldev,Tripathi, Anil. K.,Mukherjee, Debaraj
p. 11023 - 11028
(2014/03/21)