50908-04-8

Upstream product

• 1824-96-0 methyl ribofuranoside 
• 76-83-5 trityl chloride 
• 16802-02-1 methyl 2,3-didesoxy-5-O-trityl-β-D-glycero-pent-2-enofuranoside 
• 7473-45-2 1-O-methyl-D-ribofuranose 

Downstream Products

• 91102-77-1 (-)-(Methyl-5-O-trityl-2,3-didesoxy-β-D-ribofuranosido)<2,3-b>-1,4,7,10,13,16-hexaoxacyclooctadecan 
• 120090-33-7 mthyl 2,3-di-O-acetyl-5-O-trityl-β-D-ribofuranoside 
• 300583-27-1 Dodecanoic acid (2R,3R,4R,5R)-4-dodecanoyloxy-5-methoxy-2-trityloxymethyl-tetrahydro-furan-3-yl ester 
• 404918-68-9 Tetradecanoic acid (2R,3R,4R,5R)-5-methoxy-4-tetradecanoyloxy-2-trityloxymethyl-tetrahydro-furan-3-yl ester 
• 175655-96-6 methyl 3-azido-3-deoxy-2-O-(p-tolylsulfonyl)-β-D-xylofuranoside 
• 175655-97-7 (2S,3S,4R,5R)-3-Azido-5-methoxy-4-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-carboxylic acid 
• 175655-95-5 Toluene-4-sulfonic acid (2R,3R,4S,5S)-4-azido-2-methoxy-5-trityloxymethyl-tetrahydro-furan-3-yl ester 
• 137410-61-8 methyl 2-C-<(R)-carboxyethylmethyl>-2-deoxy-5-O-trityl-3,2-γ-lactone-β-D-ribofuranoside 
• 1610559-29-9 methyl 5-(trityl)-3-O-(p-toluenesulfonyl)-β-D-ribofuranoside 
• 120090-38-2 methyl 2,3-di-O-acetyl-5-O-(2,3-di-O-acetyl-5-O-benzoyl-β-D-ribofuranosyl)-β-D-ribofuranoside 
• 175655-94-4 methyl 3-azido-3-deoxy-5-O-triphenylmethyl-β-D-xylofuranoside 
• 923600-33-3 methyl 3-azido-3-deoxy-2-O-mesyl-5-O-triphenylmethyl-β-D-xylofuranoside 
• 923600-32-2 methyl 2,3-di-O-mesyl-5-O-trityl-β-D-ribofuranoside 
• 404918-73-6 Icosanoic acid (2R,3R,4R,5R)-4-icosanoyloxy-5-methoxy-2-trityloxymethyl-tetrahydro-furan-3-yl ester 

Relevant academic research and scientific papers

Structure-property relationships of ribose based ionic liquids

The authors of this work have successfully synthesized a broad choice of new ribose based ionic liquids, using several varying protecting groups (methyl, ethyl, allyl and benzyl) at the various positions of the carbohydrate, as well as different quarternised N-heterocycles and different anions. These consistent variations of the carbohydrate based ionic liquids (CHILs) enabled an extensive structure-property relationship study of thermal properties, allowing the authors to prove existing trends and to find a correlation between the decomposition temperature and the structure of the CHILs.

Manno- epi-cyclophellitols Enable Activity-Based Protein Profiling of Human α-Mannosidases and Discovery of New Golgi Mannosidase II Inhibitors

Golgi mannosidase II (GMII) catalyzes the sequential hydrolysis of two mannosyl residues from GlcNAcMan5GlcNAc2 to produce GlcNAcMan3GlcNAc2, the precursor for all complex N-glycans, including the branched N-glycans associated with cancer. Inhibitors of GMII are potential cancer therapeutics, but their usefulness is limited by off-target effects, which produce α-mannosidosis-like symptoms. Despite many structural and mechanistic studies of GMII, we still lack a potent and selective inhibitor of this enzyme. Here, we synthesized manno-epi-cyclophellitol epoxide and aziridines and demonstrate their covalent modification and time-dependent inhibition of GMII. Application of fluorescent manno-epi-cyclophellitol aziridine derivatives enabled activity-based protein profiling of α-mannosidases from both human cell lysate and mouse tissue extracts. Synthesized probes also facilitated a fluorescence polarization-based screen for dGMII inhibitors. We identified seven previously unknown inhibitors of GMII from a library of over 350 iminosugars and investigated their binding modalities through X-ray crystallography. Our results reveal previously unobserved inhibitor binding modes and promising scaffolds for the generation of selective GMII inhibitors.

Synthesis and characterization of carbohydrate-based phospholipids

Novel carbohydrate-based phospholipids containing two saturated C12 (dilauroyl ribo-phosphocholine) (DLRPC), C14 (dimyristoyl ribo-phosphocholine) (DMRPC), and C20 (diarachadonyl ribo-phosphocholine) (DARPC) carboxylic aci

Synthesis and characterization of a dianionic carbohydrate-based phospholipid.

A novel carbohydrate-based phospholipid containing a phosphatidic acid head group, bis-(2,3-lauroyl)-1-methoxy-5-ribo-phosphatidic acid (DLRPA), was synthesized and characterized by 1H NMR, 13C NMR, and 31P NMR. This molecule is an analog of dilauroyl pho

SYNTHESIS AND TRANSFORMATION OF DERIVATIVES OF THE N- AND O-GLYCOSIDES OF D-RIBOFURANOIC ACID

A method was developed for the nonselective oxidation of pyrimidine nucleosides and methyl β-D-ribofuranoside to the uronic acids by successive treatment first with triphenylchloromethane and then with acetic anydride in pyridine, followed by oxidation with chromic anhydride in acetone in the presence of sulfuric acid.The transformations of the obtained uronic acids into anhydronucleosides by the action of phthalimide and into 3',4'-unsaturated nucleosides by the action of 1,5-diazabicycloundec-5-ene are described.

New method of synthesis of D-ribose and D-lyxose

An attempt has been made to synthesize D-ribose from D-xylose using only commercial products and a minimum number of steps. D-xylose was transformed into pentenofuranoside which then was hydrolyzed. In the pyranose series, the unsaturated derivative could

Synthesis of 1,5-di-O-Acetyl-2,3,4-tri-O-n-butyl-xylo-, ribo-, and arabino-pentitols, Standards for Determination of the Configuration of Higher Sugars

The functionalization of higher sugar allylic alcohols such as 1 can be performed via either osmylation or epoxidation (followed by the opening of the oxirane ring) of the double bond.These processes should afford triols 2 of either xylo and arabino or ri

The Use of Grignard Reagents in the Synthesis of Carbohydrates. III. The One-way Anomerization of Methyl Glycofuranosides and the Opening of Their Furanose Rings

The anomerization of methyl glycofuranoside derivatives with methylmagnesium iodide or t-butylmagnesium bromide occurred in a one-way manner.For example, methyl 5-O-benzyl-β-D-ribofuranoside (3β) was converted into the corresponding α-anomer (3α) in a 95p