18311-26-7

Usage

Uses

Used in Organic Synthesis:
METHYL-6-O-TRIPHENYLMETHYL-ALPHA-D-GLUCOPYRANOSIDE is used as a chemical reagent in organic synthesis for the preparation of complex carbohydrates and other bioactive compounds. Its unique structure allows for selective reactions and modifications, facilitating the synthesis of diverse organic molecules.
Used in Laboratory Experiments:
In laboratory settings, METHYL-6-O-TRIPHENYLMETHYL-ALPHA-D-GLUCOPYRANOSIDE serves as a valuable chemical reagent for conducting various experiments. Its properties make it suitable for studying carbohydrate chemistry, enzymatic reactions, and other biochemical processes.
Used as a Protecting Group in Carbohydrate Chemistry:
METHYL-6-O-TRIPHENYLMETHYL-ALPHA-D-GLUCOPYRANOSIDE is used as a protecting group for the hydroxyl groups on glucose molecules during chemical reactions. This protects the hydroxyl groups from unwanted side reactions, allowing for selective modification of other functional groups on the molecule.
Used in Studying Carbohydrate-Protein Interactions:
METHYL-6-O-TRIPHENYLMETHYL-ALPHA-D-GLUCOPYRANOSIDE is utilized as a tool in researching carbohydrate-protein interactions, which are crucial for understanding various biological processes. The unique structure of METHYL-6-O-TRIPHENYLMETHYL-ALPHA-D-GLUCOPYRANOSIDE allows for the investigation of specific binding sites and interactions between carbohydrates and proteins.
Used in Pharmaceutical Industry:
METHYL-6-O-TRIPHENYLMETHYL-ALPHA-D-GLUCOPYRANOSIDE is used as an intermediate in the synthesis of pharmaceutical compounds. Its ability to form complex carbohydrates and other bioactive molecules makes it a valuable component in the development of new drugs and therapeutic agents.
Used in Biochemical Research:
In the field of biochemical research, METHYL-6-O-TRIPHENYLMETHYL-ALPHA-D-GLUCOPYRANOSIDE is employed for studying the structure and function of carbohydrates in biological systems. Its unique properties enable researchers to gain insights into carbohydrate metabolism, signaling pathways, and other related processes.

InChI:InChI=1/C26H28O6/c1-30-25-24(29)23(28)22(27)21(32-25)17-31-26(18-11-5-2-6-12-18,19-13-7-3-8-14-19)20-15-9-4-10-16-20/h2-16,21-25,27-29H,17H2,1H3

Upstream product

• 76-83-5 trityl chloride 
• 3396-99-4 methyl α-D-galactopyranoside 
• 86172-85-2 methyl 3,6-di-O-trityl-α-D-galactopyranoside 
• 86172-84-1 (2R,3R,4S,5R,6S)-6-Methoxy-5-trityloxy-2-trityloxymethyl-tetrahydro-pyran-3,4-diol 
• 53685-07-7 Methyl 3,4-O-isopropylidene-6-O-triphenylmethyl-α-D-galactopyranoside 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 87591-35-3 Methyl 2,3,4-tri-O-acetyl-6-O-trityl-β-D-galactopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 86179-47-7 2,6-di-O-trityl-α-D-glucopyranoside 
• 86172-75-0 (2S,3R,4R,5S,6R)-2-Methoxy-5-trityloxy-6-trityloxymethyl-tetrahydro-pyran-3,4-diol 
• 81788-19-4 (2R,3S,4S,5R,6S)-6-Methoxy-5-trityloxy-2-trityloxymethyl-tetrahydro-pyran-3,4-diol 
• 492-62-6 alpha-D-glucopyranose 
• 604-70-6 Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yl ester 
• 100-52-7 benzaldehyde 

Downstream Products

• 18685-19-3 methyl 2,3,4-tri-O-benzyl-6-O-trityl-α-D-galactopyranoside 
• 38982-56-8 methyl 2,3,4-tri-O-acetyl-6-O-trityl-α-D-galactopyranoside 
• 808148-61-0 Pent-4-enoic acid (2R,3S,4S,5R,6S)-6-methoxy-4,5-bis-pent-4-enoyloxy-2-trityloxymethyl-tetrahydro-pyran-3-yl ester 
• 799269-19-5 methyl 6-O-trityl-2,3,4-tri-O-(p-toluoyl)-α-D-galactopyranoside 
• 794525-42-1 methyl 2,3,4-tri-O-(p-toluoyl)-α-D-galactopyranoside 
• 7432-72-6 Methyl 2,3,4-tri-O-acetyl-α-D-galactopyranoside 
• 76-84-6 triphenylmethyl alcohol 
• 4356-80-3 methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside 
• 164323-13-1 (2S,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-carboxylic acid 
• 83075-41-6 methyl (methyl 2,3,4-tri-O-benzyl-α-D-galactopyranosid)uronate 
• 5155-54-4 methyl (methyl α-D-galacturonopyranoside)uronate 
• 114926-27-1 (2S,3S,4S)-1-(benzylamino)-2,3,4-tri-(benzyloxy)-5-hexene 

Relevant academic research and scientific papers

Sugar derivatives as new 6-phosphogluconate dehydrogenase inhibitors selective for the parasite Trypanosoma brucei

Sugar derivatives mimicking compounds which take part in the catalysed reaction have been assayed as alternative substrates and/or competitive inhibitors of 6-phosphogluconate dehydrogenase from Trypanosoma brucei and sheep liver. Phosphonate analogues ha

A Carbohydrate-Derived Splice Modulator

Small-molecule splice modulators have recently been recognized for their clinical potential for diverse cancers. This, combined with their use as tools to study the importance of splice-regulated events and their association with disease, continues to fue

Ring-opening polymerization of lactones using binaphthyl-diyl hydrogen phosphate as organocatalyst and resulting monosaccharide functionalization of polylactones

Binaphthyl-diyl hydrogen phosphate has been assessed for the first time as a catalyst for the ring-opening polymerization of ε-caprolactone (CL) and δ-valerolactone (VL). In the presence of benzyl alcohol as coinitiator at 40-60 °C, the polymerization is

Synthesis and characterization of methyl 6-O-alpha- and -beta-D-galactopyranosyl-beta-D-galactopyranoside.

Sequential tritylation, acetylation and detritylation of methyl beta-D-galactopyranoside gave crystalline methyl 2,3,4-tri-O-acetyl-beta-D-galactopyranoside (4) and methyl 2,3,6-tri-O-acetyl-beta-D-galactopyranoside, the latter being the minor product resulting from acetyl migration. Reaction of 4 with 2,3,4,6-tetra-O-acetyl-alpha-D-galactosyl bromide in benzene, in the presence of mercuric cyanide and mercuric bromide, gave the alpha- and beta-D-(1----6)-linked disaccharides (7 and 9, respectively) in high yield, and their structure was confirmed by 1H- and 13C-n.m.r. 1d. and 2d. spectroscopy. O-Deacetylation of 7 gave the hitherto unknown, crystalline methyl 6-O-alpha-D-galactopyranosyl-beta-D-galactopyranoside. O-Deacetylation of 9 gave the corresponding, beta-D-linked disaccharide methyl glycoside, the physical constants of which are discussed with respect to controversial data in the literature.

Peptide-Coated Platinum Nanoparticles with Selective Toxicity against Liver Cancer Cells

Peptide-stabilized platinum nanoparticles (PtNPs) were developed that have significantly greater toxicity against hepatic cancer cells (HepG2) than against other cancer cells and non-cancerous liver cells. The peptide H-Lys-Pro-Gly-dLys-NH2 was identified by a combinatorial screening and further optimized to enable the formation of water-soluble, monodisperse PtNPs with average diameters of 2.5 nm that are stable for years. In comparison to cisplatin, the peptide-coated PtNPs are not only more toxic against hepatic cancer cells but have a significantly higher tumor cell selectivity. Cell viability and uptake studies revealed that high cellular uptake and an oxidative environment are key for the selective cytotoxicity of the peptide-coated PtNPs.

Chemoenzymatic synthesis of 3-deoxy-3-fluoro-l-fucose and its enzymatic incorporation into glycoconjugates

The first synthesis of 3-deoxy-3-fluoro-l-fucose is presented, which employs ad- tol-sugar translation strategy, and involves an enzymatic oxidation of 3-deoxy-3-fluoro-l-fucitol. Enzymatic activation (FKP) and glycosylation using an α-1,2 and an α-1,3 fu

Synthesis of novel carbohydrate based pyridinium ionic liquids and cytotoxicity of ionic liquids for mammalian cells

The large pool of naturally occurring carbohydrates with their diversity in chirality and structure led to the idea of a systematic investigation of carbohydrate based ILs. To this end, we investigated the influence of different ether groups, mainly methyl or ethyl ether, on the secondary OH groups as well as different configurations on physical properties such as melting point, thermostability and especially the influence on cell toxicity. For this investigation we chose α- and β-methyl-, β-allyl- and β-phenyl d-glucopyranose as well as four 1-deoxy-pentoses. In order to be able to classify the results, more ionic liquids with different structural motives were examined for cytotoxicity. Here, we present data that confirm the biocompatibility of such ILs consisting of naturally occurring molecules or their derivatives. The synthesized carbohydrate based ILs were tested for their suitability as additives in coatings for medical applications such as drug-eluting balloons.

Chemical synthesis and preliminary biological evaluation of C-6-O-methyl-1-deoxynojirimycin as a potent α-glucosidase inhibitor

A facile and efficient synthesis of 6-O-methyl-1-deoxynojirimycin 4 from commercially available methyl α-D-glucopyranoside in 10 steps and 25% overall yield was reported. The synthetic strategy was based on the regioselective protection/deprotection at 6-

A Potent Mimetic of the Siglec-8 Ligand 6’-Sulfo-Sialyl Lewisx

Siglecs are members of the immunoglobulin gene family containing sialic acid binding N-terminal domains. Among them, Siglec-8 is expressed on various cell types of the immune system such as eosinophils, mast cells and weakly on basophils. Cross-linking of Siglec-8 with monoclonal antibodies triggers apoptosis in eosinophils and inhibits degranulation of mast cells, making Siglec-8 a promising target for the treatment of eosinophil- and mast cell-associated diseases such as asthma. The tetrasaccharide 6’-sulfo-sialyl Lewisx has been identified as a specific Siglec-8 ligand in glycan array screening. Here, we describe an extended study enlightening the pharmacophores of 6’-sulfo-sialyl Lewisx and the successful development of a high-affinity mimetic. Retaining the neuraminic acid core, the introduction of a carbocyclic mimetic of the Gal moiety and a sulfonamide substituent in the 9-position gave a 20-fold improved binding affinity. Finally, the residence time, which usually is the Achilles tendon of carbohydrate/lectin interactions, could be improved.

Visible Light Enables Aerobic Iodine Catalyzed Glycosylation

A versatile protocol for light induced catalytic activation of thioglycosides using iodine as an inexpensive and readily available photocatalyst was developed. Oxygen serves as a green and cost-efficient terminal oxidant and irradiation is performed with a common household LED-bulb. The scope of this glycosylation protocol was investigated in the synthesis of O-glycosides with yields up to 95 %.