10343-15-4Relevant academic research and scientific papers
Iron(III) chloride catalyzed glycosylation of peracylated sugars with allyl/alkynyl alcohols
Narayanaperumal, Senthil,Da Silva, Rodrigo Ce?sar,Monteiro, Julia L.,Corre?a, Arlene G.,Paixa?o, Ma?rcio W.
, p. 1982 - 1988 (2012)
In this work, the use of ferric chloride as an efficient catalyst in glycosylation reactions of sugars in the presence of allyl and alkynyl alcohols is described. The corresponding glycosides were obtained with moderate to good yields. This new procedure presented greater selectivity when compared to classic methods found in the literature. Principal features of this simple method include non-hazardous reaction conditions, low-catalyst loading, good yields and high anomeric selectivity.
Synthesis of a glycodendrimer incorporating multiple mannosides on a glucoside core
Wang, Chao,Sanders, Brian,Baker, David C.
, p. 959 - 963 (2011)
The synthesis of a glycodendrimer by incorporating repetitive mannoside units onto a glucoside core was carried out to multivalently probe fundamental carbohydrate-protein interactions. The dendritic structure was constructed by a modified procedure that
Synthesis of the allelochemical alliarinoside present in garlic mustard (Alliaria petiolata), an invasive plant species in North America
Olsen, Carl Erik,M?ller, Birger Lindberg,Motawia, Mohammed Saddik
, p. 13 - 16 (2014)
The allelochemical alliarinoside present in garlic mustard (Alliaria petiolata), an invasive plant species in North America, was chemically synthesized using an efficient and practical synthetic strategy based on a simple reaction sequence. Commercially available 1,2,3,4,6-penta-O-acetyl- β-d-glucopyranose was converted into prop-2-enyl 2,3,4,6-tetra-O-acetyl- β-d-glucopyranoside and subjected to epoxidation. In a one-pot reaction, ring-opening of the epoxide using TMSCN under solvent free conditions followed by treatment of the formed trimethylsilyloxy nitrile with pyridine and phosphoryl chloride, afforded the acetylated β-unsaturated nitriles (Z)-4-(2,3,4,6-tetra-O-β-d-glucopyranosyloxy)but-2-enenitrile and its isomer (E)-4-(23,4,6-tetra-O-β-d-glucopyranosyloxy)but-2-enenitrile. Deacetylation of Z- and/or E-isomers afforded the target molecules alliarinoside and its isomer.
A practical synthesis of 2,3,4,6-Tetra-O-acetyl-1-O-(2-propenyl)-β-D- glucopyranoside using ZnCl2
Yuasa, Yoko,Yuasa, Yoshifumi
, p. 405 - 407 (2004)
2,3,4,6-Tetra-O-acetyl-1-O-(2-propenyl)-β-D-glucopyranoside (1a), which is a useful raw material in the synthesis of a bioactive agent, has been synthesized in 50% yield by reacting β-D-glucose pentaacetate and 3 mol equiv of an allyl alcohol with 0.9 mol equiv of ZnCl2 in toluene at 80°C for 2 h followed by recrystallization from diisopropyl ether. This method is suitable for the large-scale preparation of 1a due to its efficiency, safety, and cost-effectiveness.
Mannose/glucose-functionalized dendrimers to investigate the predictable tunability of multivalent interactions
Wolfenden, Mark L.,Cloninger, Mary J.
, p. 12168 - 12169 (2005)
G4-, G5-, and G6-PAMAM dendrimers were functionalized with mixtures of mannose and glucose in varying ratios, and the relative affinities of these compounds for Concanavalin A (Con A) were evaluated using the hemagglutination assay. As the ratio of mannose to glucose increases, the relative activity in the hemagglutination assay (on a per sugar basis) increases linearly. Methyl mannose binds to Con A with an affinity 4-fold higher than that of methyl glucose; multivalency amplifies this trend. The mannose/glucose-functionalized dendrimer results reported here suggest that the affinity of multivalent associations can be attenuated in predictable, reliable ways based on monovalent affinities of the ligands. Copyright
A cyanoallyl glucoside from Alliaria petiolata, as a feeding deterrent for larvae of Pieris napi oleracea
Haribal, Meena,Yang, Zhicai,Attygalle, Athula B.,Renwick, J. Alan A.,Meinwald, Jerrold
, p. 440 - 443 (2001)
Alliarinoside, a feeding inhibitor against early instar larvae of Pieris napi oleracea, was isolated from the foliage of Alliaria petiolata and characterized as (2Z)-4-(β-D-glucopyranosyloxy)-2-butenenitrile (1) by spectroscopic methods. The structural assignment was confirmed by synthesis of peracetylated alliarinoside (2) and its 2E isomer (3). A sample of synthetic 1 was isolated by preparative HPLC from the hydrolysis of the 2Z acetate. Feeding inhibition assays showed comparable activity for the synthetic and natural glycosides.
Preparation and characterization of N-chitosan derivatives
Holme, Kevin R.,Hall, Laurance D.
, p. 291 - 306 (1992)
Allyl glycosides of 8 simple sugars have been prepared and characterized, including 1H-and 13C-NMR assignments.Formylmethyl glycosides, obtained by reductive ozonolysis of the allyl glycosides, have been reductively N-alkylated to chitosan with typical yields of 80percent.The glycosides of α- and β-D-glucopyranose, α- and β-D-galactopyranose, 2-acetamido-2-deoxy-α- and β-D-glucopyranose, β-D-glucuronic acid, and β-lactose have been incorporated by this method.The degree of substitution (d.s.) of the products was controlled by varying the molar ratio of glycoside to free amine groups of chitosan by between 0.5 and 3.0.Derivatives of degree of substitution >0.3 were typically water soluble, and compounds of higher d.s. generally gave less-viscous aqueous solutions.Assignment of 13C-NMR chemical shifts verified the structure of these derivatives.The linewidths of the branch resonances (5-100 Hz) provided qualitative information about the relationship between d.s. and branch mobility.The resonances of high-d.s. products were narrower and more intense than analogous low-d.s. derivatives.The chitosan resonances of the backbone were generally broader (50-200 Hz) and less intense, and as a result were difficult to assign fully.
Spin-labelled glycolipid analogues: D-glucose series
Tronchet,Zsely,Geoffroy
, p. 245 - 258 (1995)
Neoglycolipids bearing a paramagnetic probe in their lipophilic aglycon have been prepared. All belong to the D-glucose series, both anomers for the glucoside representatives, respectively β and α anomers in the S- and C-glucosyl series. Two different types of radical sites have been used, a relatively short-lived imino N-oxyl group for glucosides and a more stable N-acylamino N-oxyl moiety in the other cases. EPR spectra of these radical species afforded information on the conformation of the lipophilic chain in the vicinity of the paramagnetic probe.
Photoinduced Thiol-ene Chemistry Applied to the Synthesis of Self-Assembling Elastin-Inspired Glycopeptides
Piccirillo, Germano,Pepe, Antonietta,Bedini, Emiliano,Bochicchio, Brigida
, p. 2648 - 2659 (2017)
Synthetic (glyco)peptides inspired by proteins able to self-assemble are appealing biomaterials in the field of tissue engineering and regenerative medicine. Herein, for the first time, taking advantage of thiol-ene chemistry coupled to solid-phase peptide synthesis, a self-assembling peptide inspired by elastin protein was bioconjugated to three carbohydrates in order to obtain the corresponding glycopeptides. They were studied at the molecular and supramolecular level. The results show that the carbohydrate influences the molecular conformation of the glycopeptide and its self-aggregation properties as well. As future perspective, the results could enable us to tune the final self-aggregation properties of the glycopeptide by changing the sugar moiety.
A highly diastereoselective, practical synthesis of allyl, propargyl 2,3,4,6-tetra-O-acetyl-β-D-gluco, β-D-galactopyranosides and allyl, propargyl heptaacetyl-β-D-lactosides
Mereyala, Hari Babu,Gurrala, Srinivas Reddy
, p. 351 - 354 (1998)
Commercially available β-D-glucopyranose pentaacetate, β-D- galactopyranose pentaacetate and β-D-lactose heptaacetate were reacted with propargyl alcohol in the presence of BF3-Et2O catalyst to obtain in high yield and selectivity, the corresponding propargyl derivatives, respectively. These were hydrogenated by use of Lindlar catalyst to give the corresponding allyl β-D-glycopyranosides in quantitative yield.
