27299-05-4

Upstream product

• 186581-53-3 diazomethane 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 3013-58-9 methyl 4,6-O-benzylidene-2,3-di-O-methyl-α-D-glucopyranoside 
• 14835-44-0 methyl 4,6-O-<1-(hydroxymethyl)ethylidene>-2,3-di-O-methyl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 74-88-4 methyl iodide 
• 108379-03-9 methyl 4,6-O-cyclohexylidene-2,3-di-O-methyl-α-D-glucopyranoside 
• 3013-58-9 methyl 4,6-O-benzylidene-2,3-di-O-methyl-α,D-glucopyranoside 
• 15354-38-8 methyl 4,6-O-isopropylidene-2,3-di-O-methyl-α-D-glucopyranoside 
• 34698-05-0 methyl 2-O-methyl-β-D-galactopyranoside 
• 20908-66-1 methyl 2-O-methyl-α-D-glucopyranoside 
• 1204479-70-8 methyl 4-O-(9'-anthracenyl)methyl-6-O-p-methoxybenzyl-2,3-di-O-methyl-α-D-glucopyranoside 
• 1205122-19-5 C₂₃H₂₆Cl₄O₇ 

Downstream Products

• 27299-03-2 methyl 2,3-di-O-methyl-6-O-trityl-α-D-mannopyranoside 
• 82159-71-5 methyl 2,3-di-O-methyl-6-O-p-tolylsulfonyl-α-D-mannopyranoside 
• 51016-10-5 methyl 2,3-di-O-methyl-6-O-(triphenylmethyl)-α-D-glucopyranoside 
• 142543-87-1 methyl-(O⁴,O⁶-dibenzyl-O²,O³-dimethyl-α-D-glucopyranoside) 
• 4261-27-2 2,3-di-O-methyl-D-glucose 
• 51433-21-7 1,2,3-tri-O-methyl-α-D-glucopyranuronic acid methyl ester 
• 108884-73-7 methyl O²,O³-dimethyl-O⁴,O⁶-phenylboranediyl-α-D-glucopyranoside 
• 3013-58-9 methyl 4,6-O-benzylidene-2,3-di-O-methyl-α,D-glucopyranoside 
• 56586-54-0 methyl 4,6-O-benzylidene-2,3-di-O-methyl-α-D-glucopyranoside 
• 72333-35-8 methyl 4,6-O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosylidene)-2,3-di-O-methyl-α-D-glucopyranoside 
• 108800-90-4 methyl 4,6-O-<1-(methoxymethyl)ethylidene>-2,3-di-O-methyl-α-D-glucopyranoside 
• 84799-57-5 (2R,4aR,6S,7R,8S,8aR)-6,7,8-Trimethoxy-2-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 
• 85194-37-2 methyl 2,3-di-O-methyl-6-O-(methoxymethylphenyl)methyl-α-D-glucopyranoside 
• 15354-37-7 (2R,4aR,6S,7R,8S,8aS)-6,7,8-Trimethoxy-2-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 

Relevant academic research and scientific papers

Synthesis of MeON-neoglycosides of digoxigenin with 6-deoxy- and 2,6-dideoxy-D-glucose derivatives and their anticancer activity

Cardiac glycosides show anticancer activities and their deoxy-sugar chains are vital for their anticancer effects. In order to study the structure-activity relationship (SAR) of cardiac glycosides toward cancers and get more potent anticancer agents, a series of MeON-neoglycosides of digoxigenin was synthesized and evaluated. First, ten 6-deoxy- and 2,6-dideoxy-D-glucopyranosyl donors were synthesized starting from methyl α-D-glucopyranoside and 2-deoxy-D-glucose. Meanwhile, the digoxigenin was obtained by acidic hydrolysis of commercially available digoxin as glycosyl acceptor. Then, a 22-member MeON-neoglycoside library of digoxigenin was successfully synthesized by neoglycosylation method. Finally, the induction of Nur77 expression and its translocation from the nucleus to cytoplasm together with cytotoxicity of these MeON-neoglycosides were evaluated. The SAR analysis revealed that C3 glycosylation is required for their induction of Nur77 expression. Moreover, some MeON-neoglycosides (2b and 8b) could significant induce the expression of Nur77 and its translocation from the nucleus to cytoplasm. However, these compounds showed no inhibitory effects on the proliferation of cancer cells, suggesting that they may not induce apoptosis of NIH-H460 cancer cells and their underlying potential and application toward cancer cells deserves future study.

USE OF CO2 FOR THE SYNTHESIS OF CYCLIC GLYCOCARBONATES AND LINEAR POLYGLYCOCARBONATES BY POLYCONDENSATION FROM GLYCANS

Provided herein are methods for synthesizing cyclic carbonates, glycocarbonates, and polyglycocarbonates by reacting polyol glycans with carbon dioxide. Synthesis can include selective polycondensation of polyol glycan hydroxyl moieties.

From d-glucuronic acid to l-iduronic acid derivatives via a radical tandem decarboxylation-cyclization

A synthesis to l-iduronic derivatives, major components of heparin derived pentasaccharides was accomplished by formal inversion of configuration at C-5 of a d-glucuronic acid derivative through radical formation at C-5 using Barton decarboxylation followed by intramolecular radical addition on an acetylenic tether at O-4 giving exclusively a bicyclic sugar of l-ido configuration. Oxidation and ring opening of this bicyclic sugar led to a l-iduronate. This method opens the way to short syntheses of pentasaccharidic moiety of Idraparinux and congeners.

Process of preparation of L-iduronic acid comprising a decarboxylation/intramolecular cyclisation tandem reaction

The present invention relates to a process of preparation of L-iduronic acid and derivatives comprising a decarboxylation/intramolecular cyclisation tandem reaction. The present invention also relates to the intermediates of the process, as well as their use as intermediates in the preparation of Idraparinux.

Polycarbonates derived from glucose via an organocatalytic approach

An organocatalyzed ring-opening polymerization methodology was developed for the preparation of polycarbonates derived from glucose as a natural product starting material. The cyclic 4,6-carbonate monomer of glucose having the 1, 2, and 3 positions methyl-protected was prepared in three steps from a commercially available glucose derivative, and the structure was confirmed by means of NMR and IR spectroscopies, electrospray ionization mass spectrometry (MS), and single-crystal X-ray analysis. Polymerization of the monomer, initiated by 4-methylbenzyl alcohol in the presence of 1,5,7-triazabicyclo[4.4.0]dec-5-ene as the organocatalyst, proceeded effectively in a controlled fashion to afford the polycarbonate with a tunable degree of polymerization, narrow molecular weight distribution, and well-defined end groups, as confirmed by a combination of NMR spectroscopy, gel-permeation chromatography, and MALDI-TOF MS. A distribution of head-to-head, head-to-tail, and tail-to-tail regiochemistries was determined by NMR spectroscopy and tandem MS analysis by electron transfer dissociation. These polycarbonates are of interest as engineering materials because of their origination from renewable resources combined with their amorphous character and relatively high glass transition temperatures as determined by X-ray diffraction and differential scanning calorimetry studies.

Poly(d-glucose carbonate) block copolymers: A platform for natural product-based nanomaterials with solvothermatic characteristics

A natural product-based polymer platform, having the characteristics of being derived from renewable materials and capable of breaking down, ultimately, into natural byproducts, has been prepared through the ring-opening polymerization (ROP) of a glucose-based bicyclic carbonate monomer. ROP was carried out via chain extension of a polyphosphoester (PPE) macroinitiator in the presence of 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) organocatalyst to afford the PPE-b-poly(d-glucose carbonate) (PDGC) block copolymer. This new copolymer represents a functional architecture that can be rapidly transformed through thiol-yne reactions along the PPE segment into a diverse variety of amphiphilic polymers, which interestingly display stimuli-sensitive phase behavior in the form of a lower critical solution temperature (LCST). Below the LCST, they undergo self-assembly to form spherical core-shell nanostructures that display a poorly defined core-shell morphology. It is expected that hydrophobic patches are exposed within the micellar corona, reminiscent of the surface complexity of proteins, making these materials of interest for triggered and reversible assembly disassembly processes.

PROCESS OF PREPARATION OF L-IDURONIC ACID AND DERIVATIVES COMPRISING A DECARBOXYLATION/INTRAMOLECULAR CYCLISATION TANDEM REACTION

The present invention relates to a process of preparation of L-iduronic acid and derivatives comprising a decarboxylation/intramolecular cyclisation tandem reaction. The present invention also relates to the intermediates of the process, as well as their use as intermediates in the preparation of Idraparinux.

Cleavage of 4,6- O -benzylidene acetal using sodium hydrogen sulfate monohydrate

The use of protecting groups is an important protocol in carbohydrate synthesis. Among protecting groups, benzylidene acetals are generally more stable than other acetals; therefore, strong conditions are often required for deprotection. We report the deprotection of 4,6-O-benzylidene derivatives using sodium hydrogen sulfate monohydrate under mild conditions. Georg Thieme Verlag Stuttgart New York.

Enantioselective alkylation of aldehydes using dialkylzincs catalyzed by simple chiral diols derived from naturally occurring monosaccharides

Enantioselective alkylation of aldehydes was achieved in up to 84% ee using dialkylzincs catalyzed by simple diols derived from naturally occurring monosaccharides.

Hydroxy group acidities of partially protected glycopyranosides

A comprehensive acidity study of carbohydrate hydroxy groups has been carried out. Relative acidities (Ke) were determined spectrophotometrically for partially methylated methyl α-D- glycopyranosides. Apparently, the acidity is strongly affected by intramolecular hydrogen bonding as well as stereochemistry and solvation. By comparison with pKe and pKa values of aliphatic alcohols and polyols the first estimation of the pKa values for partially protected glycopyranosides was obtained. These findings contribute to the understanding of the relative reactivities of carbohydrate hydroxy groups.