Category: 130539-43-4

On January 5, 1995, Eklind, Karin Ingeborg; Loenn, Hans Roland; Tiden, Anna-Karin Ulla Edit published a patent.Recommanded Product: 130539-43-4 The title of the patent was Preparation of fucosylated glycosides as inhibitors of bacterial adherence.. And the patent contained the following:

Guanidinyl Y-Z1-R, A-Z2-R, A-Z3-B-Z4-R, A-Z5-B-Z6-C-Z7-R, A-Z8-B-Z9-C-Z10-D-Z11-R, A-Z12-B-Z13-C-Z14-D-Z15-E-Z16-R [Z1-Z16 = O, S, CH2, NR25; R25 = H, alkyl, alkenyl, alkylcarbonyl, (substituted) PhCO; A = Q1; B = Q2; C = Q3; D = Q4; E = Q5; Y = Q6; R = H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylcarbonyl, alkenylcarbonyl, (substituted) cycloalkylalkylcarbonyl, arylcarbonyl, etc.; R1-R3 = H, halo, N3, guanidinyl, alkyl, alkenyl, alkynyl, (substituted) aryl, alkoxyalkyl, etc.; R1A-R4E = R1, YZ1; with provisos], were prepd for therapy or prophylaxis in conditions involving infection by Heliobacter pylori of human gastric mucosa. Thus, Et 3-O-(tri-O-benzyl-α-L-fucopyranosyl)-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside was stirred with N-iodosuccinimide, mol. sieves, and CF3CO2H in CH2Cl2/Et2O to give 97% Me 4,6-O-benzylidene-3-O-(tri-O-benzyl-α-fucopyranosyl)-2-deoxy-2-phthalimido-β-D-glucopyranoside. This was refluxed 20 h with N2H4 in aqueous EtOH followed by acetylation of the crude product to give Me 2-acetamido-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside. The latter was hydrogenolyzed at 200 kPa over Pd/C in AcOH/EtOAc/H2O to give 90% Me 2-acetamido-2-deoxy-3-O-α-L-fucopyranosyl-D-glucopyranoside. Title compounds gave 34-93% inhibition of binding of Helicobacter pylori to human gastric tissue. Use of title compounds with various antibiotics, antacids, gastric secretion inhibitors, antigastritis drugs, and antiulcer drugs, is claimed. The experimental process involved the reaction of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside(cas: 130539-43-4).Recommanded Product: 130539-43-4

The Article related to fucosylated glycoside preparation bacterial adherence inhibitor, helicobacter pylori adhesion inhibitor fucosylated glycoside, gastric mucosa helicobacter pylori adhesion inhibitor and other aspects.Recommanded Product: 130539-43-4

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On July 8, 2002, Borbas, Aniko; Szabo, Zoltan B.; Szilagyi, Laszlo; Benyei, Attila; Liptak, Andras published an article.Synthetic Route of 130539-43-4 The title of the article was Dioxane-type (2-naphthyl)methylene acetals of glycosides and their hydrogenolytic transformation into 6-O- and 4-O-(2-naphthyl)methyl (NAP) ethers. And the article contained the following:

α-, β-D-Gluco-, galacto-, 2-deoxy-2-phthalimido-β-D-glucopyranosides with different aglycons (Me, allyl, p-methoxyphenyl, thioethyl) reacted with 2-naphthaldehyde di-Me acetal to give rise to 4,6-O-(2-naphthyl)methylene acetals. The acetals were converted into fully protected compounds bearing benzoyl, benzyl, allyl, p-methoxybenzyl groups. The fully alkylated dioxane-type acetals were hydrogenolyzed with AlH3 (3LiAlH4-AlCl3) reagent to furnish 4-O-NAP/6-OH derivatives All acetals were treated with BH3·Me3N-AlCl3 in THF and a reverse regioselectivity was observed, producing 6-O-NAP/4-OH derivatives Similar regioselectivity was also observed by using NaCNBH3-HCl reagent. In all reactions very mild reaction conditions were required, regioselectivity was better than 93:7, and the isolated yields were between 83-92%. All compounds were characterized by 1H and 13C NMR spectra. Solid-state and solution conformation of Me 2,3-di-O-acetyl-4,6-O-(2-naphthyl)methylene-α-D-galactopyranoside were elucidated by X-ray and NMR measurements. The experimental process involved the reaction of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside(cas: 130539-43-4).Synthetic Route of 130539-43-4

The Article related to naphthyl methylene acetal glycoside preparation, naphthylmethyl ether glycoside regioselective preparation, me acetyl naphthylmethylene galactopyranoside preparation crystal mol structure and other aspects.Synthetic Route of 130539-43-4

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On July 31, 1995, Nilsson, Kurt G. I.; Eliasson, Anna; Larsson-Lorek, Ulla published an article.Product Details of 130539-43-4 The title of the article was Production of glucosamine containing disaccharides of the Lewis-A and -X types employing glycosidases. And the article contained the following:

Disaccharide derivatives I and II of interest for inhibition studies and for synthesis of the blood group determinants Lewis-A and Lewis-X were obtained with glycosidases as catalysts. Thus, Fucα(1-4)(6-OBn)GlcNH2βSEt and Galβ1-3(6-OBn)GlcNH2β-SEt were produced employing (6-OBn)GlcNH2βSEt as acceptor and α-L-fucosidase and β-D-galactosidase resp., as catalysts. The phthalimido derivative of lactosamine, Galβ1-4GlcNPhthβSEt, was prepared from lactose employing GlcNPhthβSEt as the acceptor and a yeast β-galactosidase as catalyst. The reactions were both regio- and stereo-specific, which allowed straightforward production of pure products on a gram scale and higher. The experimental process involved the reaction of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside(cas: 130539-43-4).Product Details of 130539-43-4

The Article related to glucosamine oligosaccharide, stereoselective transglycosidation thio glycoside enzymic, regioselective transglycosidation thio glycoside enzymic, blood group determinant synthon oligosaccharide and other aspects.Product Details of 130539-43-4

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On May 27, 2021, Wyand, Michael; Swiss, Gerald F. published a patent.Formula: C16H19NO6S The title of the patent was Low contaminant vaccines against microbes possessing a cell wall structure comprising poly-β-(1→6)-glucosamine (PNAG). And the patent contained the following:

Disclosed are antimicrobial vaccines (A-B)x-C, wherein A comprises 3 to 12 3-(1→6)-glucosamine I (carbohydrate ligand) groups; B is a linker; C is tetatus toxoid; x is an integer from about 30 to about 39; n is an integer from 1 to 10, wherein less than about 40% of the total number of such units are N-acetylated. The experimental process involved the reaction of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside(cas: 130539-43-4).Formula: C16H19NO6S

The Article related to glucosamine pnag antimicrobial vaccine oligosaccharide preparation human fpa91, antimicrobial vaccine cell wall glucosamine oligosaccharide burn therapy, vaccine oligosaccharide glucsosamine tetanus toxoid carrier f598 monoclonal antibody and other aspects.Formula: C16H19NO6S

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On May 21, 2007, Wang, Ping; Lee, Heeseob; Fukuda, Minoru; Seeberger, Peter H. published an article.Related Products of 130539-43-4 The title of the article was One-pot synthesis of a pentasaccharide with antibiotic activity against Helicobacter pylori. And the article contained the following:

A pentasaccharide that contains the α-1,4-GlcNAc mucin core two-branched O-glycan has been synthesized by a one-pot, two-step glycosylation strategy; this particular carbohydrate motif may provide protection against Helicobacter pylori induced pathologies since the synthetic pentasaccharide inhibits cholesterol α-glucosyltransferase (IC50 of 0.47 mM). The experimental process involved the reaction of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside(cas: 130539-43-4).Related Products of 130539-43-4

The Article related to glycosylation glucosyltransferase inhibitor oligosaccharide synthesis antibacterial, cholesterol glucosyltransferase inhibitor oligosaccharide synthesis antibiotic helicobacter pylori antibacterial and other aspects.Related Products of 130539-43-4

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On July 31, 1997, Nilsson, Kurt G.I.; Pan, Hefeng; Larsson-Lorek, Ulla published an article.Recommanded Product: 130539-43-4 The title of the article was Synthesis of modified carbohydrates with glycosidases: stereo- and regiospecific syntheses of lactosamine derivatives and related compounds. And the article contained the following:

Different lactosamine derivatives, modified in the 2-N- and anomeric positions and suitable as intermediates for synthesis of Lewis-x and related compounds, were prepared with high specificity on a multigram scale directly from lactose, employing different D-glucosamine derivatives as acceptors and the abundant β-D-galactosidase from Bullera singularis as catalyst. Thus, Me O-β-D-galactopyranosyl-(1→4)-2-azido-2-deoxy-β-D-glucopyranoside, Et O-β-D-galactopyranosyl-(1→4)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside and Et O-β-D-galactopyranosyl-(1→4)-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside were formed in 20-40% yield as calculated based on added acceptor. The 2-phthalimido derivative was isolated in crystalline form without chromatog. (extraction/crystallization procedure). The trisaccharide derivative Et O-β-D-galactopyranosyl-(1→4)-O-β-D-galactopyranosyl-(1→4)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside was also isolated. The corresponding cellobiosamine derivatives were similarly obtained from cellobiose using the same type of catalyst and acceptors. The β-D-galactosidase from bovine testes was found to catalyze the highly specific formation of the β(1→6)-linked derivative Et O-β-galactopyranosyl-(1→6)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside from lactose and Et 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside. Et O-α-L-fucopyranosyl-(1→4)-2-amino-6-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside, suitable as an intermediate for preparation of Lewis-a and related compounds, was obtained from p-nitrophenyl α-L-fucopyranoside and 2-amino-6-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside, employing α-L-fucosidase from bovine testes as catalyst. The experimental process involved the reaction of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside(cas: 130539-43-4).Recommanded Product: 130539-43-4

The Article related to galactopyranosylazidodeoxyglucopyranoside fucopyranosylaminodeoxythioglucopyranoside preparation glycosidase, lactose transglycosidation galactosidase, oligosaccharide stereochem preparation glycosidase and other aspects.Recommanded Product: 130539-43-4

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On March 31, 1991, Peters, Thomas; Weimar, Thomas published an article.Formula: C16H19NO6S The title of the article was Improved synthesis of α-L-Fuc(1 → 4)-β-D-GlcNAc and α-L-Fuc(1 → 6)-β-D-GlcNAc building blocks: a convergent strategy employing 4-O → 6-O acetyl migration; NOE data on protected α-1,4-linked disaccharides. And the article contained the following:

The synthesis of the two thioethyl disaccharide building blocks I (R1 = PhCH2, R2 = Ac, R3 = phthalimido, R4 = SEt) and II (same R1-R4) was achieved via coupling of fucosyl bromide III with the acceptor alcs. IV (R5 = Ac, R6 = H) and IV (R5 = H, R6 = Ac) under in situ anomerization conditions. The selectively protected 2-deoxy-2-phthalimidoglucose derivative IV (R5 = H, R6 = Ac) was derived from by utilizing an optimized acetyl migration reaction. The thioethyl function in disaccharides I and II was activated with bromine, and excess bromine was removed with cyclohexene. The sensitive 1,6-linkage in the disaccharide I proved to be stable under these activating conditions. The disaccharide bromides I (R1 = CH2Ph, R2 = Ac, R3 = phthalimido, R4 = Br) and II (R1 = CH2Ph, R2 = Ac, R3 = phthalimidi, R4 = Br) were treated with methanol to afford after deblocking the Me glycosides I (R1 = R2 = H, R3 = AcNH, R4 = OMe) and II (R1 = R2 = H, R3 = AcNH, R4 = OMe). Homonuclear 1H-NOE data were obtained for the protected 1,4-linked disaccharide II (R1 = PhCH2, R2 = Ac, R3 = phthalimido, R4 = SEt) suggesting that its preferred solution conformation is rather similar to the solution conformation of the deblocked disaccharide II (R1 = R2 = H, R3 = AcNH, R4 = OMe) in aqueous solution as known from literature data. The experimental process involved the reaction of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside(cas: 130539-43-4).Formula: C16H19NO6S

The Article related to fucosyl bromide glycosidation thioglycoside, fucosylglucosamine thioglycoside building block, disaccharide thioglycoside building block, deoxyphthalimidoglucose glycosidation fucosyl bromide, conformation disaccharide glycoside linkage and other aspects.Formula: C16H19NO6S

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles