153658-86-7

Upstream product

• 149717-37-3 Acetic acid (3S,4R,5R,6S)-4,5-diacetoxy-2-(bis-benzyloxy-phosphanyloxy)-6-methyl-tetrahydro-pyran-3-yl ester 
• 106-45-6 para-thiocresol 
• 73-34-7 6-deoxy-L-galactose 
• 108-24-7 acetic anhydride 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-fucopyranose 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-β-L-fucopyranose 
• 6696-41-9 alpha-L-fucose 

Downstream Products

• 959774-86-8 p-methylphenyl 1-thio-β-L-fucopyranoside 
• 211801-54-6 p-methylphenyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside 
• 137063-47-9 (2',3',4'-tri-O-benzyl-α-L-fucopyranosyl)-(1→6)-methyl-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 71672-13-4 2,3,4-tri-O-benzyl-α-L-fucopyanosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 116391-15-2 methyl 2,6-di-O-benzyl-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-α-D-galactopyranoside 
• 1607433-64-6 p-tolyl 2,3-di-O-benzyl-1-thio-β-L-fucopyranoside 
• 1607433-63-5 p-Tolyl 2-O-benzyl-1-thio-β-L-fucopyranoside 
• 1607433-62-4 p-tolyl 2-O-benzyl-3,4-O-isopropylidene-1-thio-β-L-fucopyranoside 
• 1607433-78-2 p-Tolyl (4-O-benzoyl-2,3-di-O-benzyl-α-L-fucopyranosyl)-(1→ 3)-4-O-benzoyl-2-O-benzyl-1-thio-β-L-fucopyranoside 
• 1607433-71-5 p-Tolyl 4-O-benzoyl-2-O-benzyl-1-thio-β-L-fucopyranoside 
• 220645-52-3 p-methylphenyl 2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-6-O-tert-butyldiphenylsilyl-4-O-levulinyl-3-O-p-methoxybenzyl-1-thio-β-D-galactopyranoside 

Relevant academic research and scientific papers

Facile Cu(OTf)2-Catalyzed Preparation of Per-O-acetylated Hexopyranoses with Stoichiometric Acetic Anhydride and Sequential One-Pot Anomeric Substitution to Thioglycosides under Solvent-Free Conditions

Solvent-free per-O-acetylation of hexoses with a stoichiometric amount of acetic anhydride employing 0.03 mol % Cu(OTf)2 proceeded in high yields (90-99%) at room temperature to give exclusively pyranosyl products as an anomeric mixture, the α/

Deep interrogation of metabolism using a pathway-targeted click-chemistry approach

Untargeted metabolomics indicates that the number of unidentified small-molecule metabolites may exceed the number of protein-coding genes for many organisms, including humans, by orders of magnitude. Uncovering the underlying metabolic networks is essential for elucidating the physiological and ecological significance of these biogenic small molecules. Here we develop a click-chemistry-based enrichment strategy, DIMEN (deep interrogation of metabolism via enrichment), that we apply to investigate metabolism of the ascarosides, a family of signaling molecules in the model organism C. elegans. Using a single alkynemodified metabolite and a solid-phase azide resin that installs a diagnostic moiety for MS/MS-based identification, DIMEN uncovered several hundred novel compounds originating from diverse biosynthetic transformations that reveal unexpected intersection with amino acid, carbohydrate, and energy metabolism. Many of the newly discovered transformations could not be identified or detected by conventional LC-MS analyses without enrichment, demonstrating the utility of DIMEN for deeply probing biochemical networks that generate extensive yet uncharacterized structure space.

Synthesis of trisaccharide repeating unit of fucosylated chondroitin sulfate

We described the chemical synthesis of a sulfated trisaccharide repeating unit of fucosylated chondroitin sulfate (FCS), which has significant anticoagulant activity. Well-functionalized monosaccharides were readily prepared, and highly efficient glycosyl

Preparation method, intermediate and application of fucosylated chondroitin sulfate trisaccharide

The invention discloses a synthesizing method of a fucosylated chondroitin sulfate trisaccharide repeat unit. The synthesizing method takes beta-penta-acetyl glucose, D-galactosamine hydrochloride andL-fucose, which are easy to acquire, as raw materials t

Direct and Regioselective Di-α-fucosylation on the Secondary Rim of β-Cyclodextrin

A straightforward glycosylation method is described to regio- and stereoselectively introduce two α-l-fucose moieties directly to the secondary rim of β-cyclodextrin. Using NMR and MS fragmentation studies, the nonasaccharide structure was determined, which was also visualized using molecular dynamics simulations. The reported glycosylation method proved to be robust on gram-scale, and may be generally applied to directly glycosylate β-cyclodextrins to make well-defined multivalent glycoclusters.

A novel O-fucosylation strategy preactivated by (p-Tol)2SO/Tf2O and its application for the synthesis of Lewis blood group antigen Lewisa

Based on a preactivation strategy using (p-Tol)2SO/Tf2O, a new O-fucosylation method with thioglycoside as donor under mild conditions was reported. High yields and excellent α-stereoselectivities of the fucosylation were obtained wi

Stereoselective synthesis of a sulfated tetrasaccharide corresponding to a rare sequence in the galactofucan isolated from Sargassum polycystum

The first chemical synthesis of a highly sulfated tetrasaccharide 1, as the rare sequence in the galactofucan isolated from the brown alga Sargassum polycystum, was achieved in a convergent and stereoselective manner. The key features of the synthetic str

A facile and efficient method for the one-pot synthesis of per-O-acetylated thioglycosides from unprotected sugars

An efficient, convenient protocol for the preparation of per-O-acetylated p-tolylthio glycosides is described. Treatment of various unprotected sugars, including 2-deoxy-2-amino sugars, sialic acid, lactose, and maltose, with acetic anhydride using SnCl4 as a catalyst, and subsequently with p-tolylthiol, furnished the corresponding thioglycosides in 71%-90% yield under solvent-free conditions.

2,3-Anhydrosugars in glycoside bond synthesis. Application to 2,6-dideoxypyranosides

We describe here the first use of 2,3-anhydrosugars as glycosylating agents for the preparation of 2-deoxypyranosides. In particular, the methodology was used to assemble 2,6-dideoxysugar glycosides. Glycosylation of a panel of alcohols with one of two 6-

Low-concentration 12-trans β-selective glycosylation strategy and its applications in oligosaccharide synthesis

This study develops an operationally easy, efficient, and general 1,2-trans β-selective glycosylation reaction that proceeds in the absence of a C2 acyl function. This process employs chemically stable thioglycosyl donors and low substrate concentrations to achieve excellent β-selectivities in glycosylation reactions. This method is widely applicable to a range of glycosyl substrates irrespective of their structures and hydroxyl-protecting functions. This low-concentration 1,2-trans β-selective glycosylation in carbohydrate chemistry removes the restriction of using highly reactive thioglycosides to construct 1,2-trans β-glycosidic bonds. This is beneficial to the design of new strategies for oligosaccharide synthesis, as illustrated in the preparation of the biologically relevant β-(1-6)-glucan trisaccharide, β-linked Gb3 and isoGb3 derivatives.