34370-91-7

Upstream product

• 29581-48-4 O-benzyl-1,2-di-O-isopropylidene-5-O-(p-toluenesulfonyl)-α-D-xylofuranose 
• 100-39-0 benzyl bromide 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 213963-74-7 ((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-tert-butyl-diphenyl-silane 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 40429-53-6 5-O-p-toluenesulfonyl-3-O-benzyl-1,2-O-isopropylidene-β-D-arabinofuranose 
• 10323-20-3 D-Arabinose 
• 167500-61-0 3-O-benzyl-5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-xylofuranose 
• 253596-65-5 3-O-benzyl-5-deoxy-5-C-[benzyl 2,3,4-tri-O-benzyl-7-deoxy-D-glycero-α-D-manno-heptopyranosid-7(E)-ylidene]-1,2-O-isopropylidene-α-D-xylofuranose 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 185541-37-1 1,2-O-isopropylidene-3-O-benzyl-5-O-triphenylmethyl-α-D-xylofuranoside 
• 126308-97-2 (3aR,5R,6S,6aR)-6-Benzyloxy-5-(3,4-dimethoxy-benzyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole 
• 23558-05-6 3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose 
• 42926-89-6 1,2-O-isopropylidene-3-O-benzyl-α-D-glucofuranose 

Downstream Products

• 117661-89-9 3-O-benzyl-1,2-O-isopropylidene-5-O-trifluoromethanesulphonyl-α-D-xylofuranose 
• 29580-99-2 (3aR,4S,5R,6aR)-4-(benzyloxy)-5-(iodomethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole 
• 87060-31-9 (3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-octadecyloxymethyl-tetrahydro-furo[2,3-d][1,3]dioxole 
• 80229-19-2 methyl 3-O-benzyl-α-D-xylo-pentofuranoside 
• 174833-50-2 methyl 3-O-benzyl-β-D-xylo-pentofuranoside 
• 23558-05-6 3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose 
• 19139-83-4 3-O-Benzyl-xylit 
• 1146540-67-1 3-O-benzyl-5-O-dibenzylphosphono-1,2-O,O-isopropylidene-α-D-xylofuranose 
• 1206111-46-7 3-O-benzyl-1,2-O-isopropylidene-5-O-(4-methoxyphenyl)-α-D-xylofuranose 
• 1373283-23-8 2-(3-O-benzyl-1,2-O-isopropylidene-5-deoxy-α-D-xylo-1,4-furanosyl)-2,3-dihydro-4H-pyran-4-one 
• 1373283-21-6 2-(3-O-benzyl-1,2-O-isopropylidene-5-deoxy-α-D-xylo-1,4-furanosyl)-2,3-dihydro-4H-pyran-4-one 
• 18439-45-7 3-O-Benzyl-6-desoxy-1,2-O-isopropyliden-α-D-gluco-hexofuranose 
• 76801-66-6 5-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexodialdo-1,4-furanose 
• 57575-19-6 2-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethanol 

Relevant academic research and scientific papers

Gram-level total synthesis method of sulfur onium salt type natural product neoponkoranol extracted from salacia plants

The invention belongs to the field of chemical synthesis and particularly relates to a gram-level total synthesis method of a sulfur onium salt type natural product neoponkoranol with hypoglycemic activity extracted from salacia plants. According to the m

Synthesis of Benz-Fused Azoles via C-Heteroatom Coupling Reactions Catalyzed by Cu(I) in the Presence of Glycosyltriazole Ligands

Glycosyl triazoles are conveniently accessible and contain multiple metal-binding units that may assist in metal-mediated catalysis. Azide derivatives of d-glucose have been converted to their respective aryltriazoles and screened as ligands for the synthesis of 2-substituted benz-fused azoles and benzimidazoquinazolinones by Cu-catalyzed intramolecular Ullmann type C-heteroatom coupling. Good to excellent yields for a variety of benz-fused heterocyles were obtained for this readily accessible catalytic system.

Visible-Light-Mediated, Chemo- and Stereoselective Radical Process for the Synthesis of C-Glycoamino Acids

An approach for efficient synthesis of C-glycosyl amino acids is described. Different from typical photoredox-catalyzed reactions of imines, the new process follows a pathway in which α-imino esters serve as electrophiles in chemoselective addition reactions with nucleophilic glycosyl radicals. The process is highlighted by the mild nature of the reaction conditions, the highly stereoselectivity attending C-C bond formation, and its applicability to C-glycosylations using both armed and disarmed pentose and hexose derivatives.

Furan glucosyl triazole type compound and preparation method and bactericide thereof

The invention relates to the field of bactericidal compounds, in particular to a furan glucosyl triazole type compound and a preparation and a bactericide thereof. The molecular formula of the furan glucosyl triazole type compound is shown in the following description, wherein R1 is methyl or benzyl, and R2 are phenyl and derivative of the phenyl or ethyl derivatives. Based on structural characteristics of the substrate fructose-6-phosphate and an ISOM catalytic hypothesis mechanism, the inventor adopts a five-membered furan glucose derivative with a similar structure as a basic skeleton, introduces an effective active group triazole structure of pesticides, designs a series of novel furan glucosyl triazole type compounds for the first time, studies the biological activities of the furan glucosyl triazole type compound, examines structure-activity relationships of the furan glucosyl triazole type compound, and lays the foundation for selecting better inhibitors.

Furanosyl Nucleoside Analogues Embodying Triazole or Theobromine Units as Potential Lead Molecules for Alzheimer's Disease

The synthesis of novel types of furanosyl nucleoside analogues, namely N-(benzyltriazolyl)methyl glucuronamide derivatives, N-dodecyl glucuronamide-based phenyltriazole nucleosides, and theobromine xylosyl 5′-isonucleosides, as potential cholinesterase in

Active Site Mapping of Xylan-Deconstructing Enzymes with Arabinoxylan Oligosaccharides Produced by Automated Glycan Assembly

Xylan-degrading enzymes are crucial for the deconstruction of hemicellulosic biomass, making the hydrolysis products available for various industrial applications such as the production of biofuel. To determine the substrate specificities of these enzymes, we prepared a collection of complex xylan oligosaccharides by automated glycan assembly. Seven differentially protected building blocks provided the basis for the modular assembly of 2-substituted, 3-substituted, and 2-/3-substituted arabino- and glucuronoxylan oligosaccharides. Elongation of the xylan backbone relied on iterative additions of C4-fluorenylmethoxylcarbonyl (Fmoc) protected xylose building blocks to a linker-functionalized resin. Arabinofuranose and glucuronic acid residues have been selectively attached to the backbone using fully orthogonal 2-(methyl)naphthyl (Nap) and 2-(azidomethyl)benzoyl (Azmb) protecting groups at the C2 and C3 hydroxyls of the xylose building blocks. The arabinoxylan oligosaccharides are excellent tools to map the active site of glycosyl hydrolases involved in xylan deconstruction. The substrate specificities of several xylanases and arabinofuranosidases were determined by analyzing the digestion products after incubation of the oligosaccharides with glycosyl hydrolases.

Stereodivergent synthesis of right- and left-handed iminoxylitol heterodimers and monomers. Study of their impact on β-glucocerebrosidase activity

A library of dimers and heterodimers of both enantiomers of 2-O-alkylated iminoxylitol derivatives has been synthesised and evaluated on β-glucocerebrosidase (GCase), the enzyme responsible for Gaucher disease (GD). Although the objective was to target simultaneously the active site and a secondary binding site of the glucosidase, the (-)-2-iminoxylitol moiety seemed detrimental for imiglucerase inhibition and no significant enhancement was obtained in G202R, N370S and L444P fibroblasts. However, all compounds having at least one (+)-2-O-alkyl iminoxylitol are GCase inhibitors in the nano molar range and are significant GCase activity enhancers in G202R fibroblats, as confirmed by a decrease of glucosylceramide levels and by co-localization studies.

Total synthesis of cephalosporolide E via a tandem radical/polar crossover reaction. The use of the radical cations under nonoxidative conditions in total synthesis

The present work reports the first example of the use of the chemistry of radical cations under nonoxidative conditions in total synthesis. Using a late-stage tandem radical/polar crossover reaction, a highly stereoselective total synthesis of cephalospor

Synthetic and Immunological Studies of Mycobacterial Lipoarabinomannan Oligosaccharides and Their Protein Conjugates

Lipoarabinomannan (LAM) is one of the major constituents of the Mycobacterium tuberculosis cell wall and an attractive molecular scaffold for antituberculosis drug and vaccine development. In this paper, a convergent strategy was developed for the synthes

Titanocene dihalides and ferrocenes bearing a pendant α-d- xylofuranos-5-yl or α-d-ribofuranos-5-yl moiety. synthesis, characterization, and cytotoxic activity

Titanocene dichlorides of general formula [(η5-C 5H5)(η5-C5H4R) TiCl2] (where R = 5-deoxy-1,2-di-O-isopropylidene-3-O-benzyl-α- d-xylofuranos-5-yl (Xylf) (8a); R = 5-deoxy-1,2-di-O-isopropylidene-3-O-benzyl- α-d-ribofuranos-5-yl (Ribf) (8b)) and [(η5-C 5H4R)2TiCl2] (R = Xylf (9a); R = Ribf (9b)) were prepared by reaction of the corresponding lithium cyclopentadienides 7a,b with an equimolar amount of [(η5-C 5H5)TiCl3] or a 0.5 mol amount of [TiCl 4(THF)2]. Titanocene difluorides of the general formula [(η5-C5H4R1)(η5- C5H4R2)TiF2] (R1 = H and R2 = Ribf (10); R1 = R2 = Xylf (11a); R 1 = R2 = Ribf (11b)) were obtained by fluorination of the corresponding titanocene dichlorides 8b and 9 with the fluorinating agent {2-(CH2NMe2)C6H4-κC,N}(n-Bu) 2SnF in high yields. Alternatively, complexes 11 were prepared in a straightforward way by direct reaction of [TiF4(THF)2] with 2 equiv of the corresponding lithium cyclopentadienide 7a,b. Ferrocene complexes [(η5-C5H4R)2Fe] (R = Xylf (12a); R = Ribf (12b)) were synthesized by metathesis of 2 equiv of lithium cyclopentadienide 7a,b and 1 equiv of anhydrous FeCl2. Deprotection of the benzyl group in ferrocenes 12 proceeded cleanly by a catalytic hydrogenation on Pd/C and afforded the ferrocene diols [(η5- C5H4R)2Fe] (R = 5-deoxy-1,2-di-O- isopropylidene-α-d-xylofuranos-5-yl (Xylf-OH) (14a); R = 5-deoxy-1,2-di-O-isopropylidene-α-d-ribofuranos-5-yl (Ribf-OH) (14b)). A scaled up benzyl deprotection with Et3SiH as a hydrogen source led to the replacement of only one benzyl group, which gave the ferrocene alcohol [(η5-C5H4R1)(η5- C5H4R2)Fe] (R1 = Xylf and R 2 = Xylf-OH (13)). The prepared complexes were characterized by elemental analysis, melting point determination, NMR, IR, and ESI-MS, and the molecular structure of 9b was determined by X-ray diffraction analysis. The cytotoxic activity of complexes 8-14 against A2780 and A2780cis cancer cells was evaluated by MTT tests. Titanocene difluorides 10 and 11 and ferrocene diol 14a showed cytotoxicity against A2780 cells in the medium to low micromolar range, while the most active species, 11b, displayed about 40% higher cytotoxicity against A2780cis in comparison to a cisplatin standard.