70831-62-8

Upstream product

• 4119-19-1 Methyl-(2,3-di-O-benzyl-5-O-trityl-α-L-arabinofuranosid) 
• 4060-35-9 methyl 5-O-trityl-α-D-arabinofuranoside 
• 10323-20-3 D-Arabinose 
• 79083-42-4 methyl D-arabinofuranoside 
• 1360561-10-9 C₃₆H₄₂O₅Si 
• 56607-40-0 methyl D-arabinofuranoside 
• 532401-39-1 methyl 2,3-di-O-benzyl-α-D-ribofuranoside 
• 1251531-61-9 Methyl 2,3 di-O-benzyl-5-O-trityl-D-ribofuranoside 
• 1824-96-0 methyl ribofuranoside 
• 532-20-7 D-Ribose 
• 70797-90-9 (2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-trityloxymethyl-tetrahydro-furan 
• 124648-93-7 (2S,3R,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-trityloxymethyl-tetrahydro-furan 
• 532401-38-0 methyl 6-O-trityl-α,β-ribofuranoside 

Downstream Products

• 697298-48-9 methyl 2,3-di-O-benzyl-5-dehydro-α-D-arabinofuranoside 
• 402758-96-7 methyl 5-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2,3-di-O-benzyl-α-D-arabinofuranoside 
• 402758-90-1 methyl 2,3-di-O-benzyl-5-O-(2-O-benzoyl-3,5-di-O-benzyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside 
• 492470-86-7 (2S,3S,4S,5S)-3,4-Bis-benzyloxy-2-iodomethyl-5-methoxy-tetrahydro-furan 
• 527681-52-3 methyl 5-O-benzoyl-(2,3-anhydro-β-D-lyxofuranosyl)-2,3-di-O-benzyl-α-D-arabinofuranoside 
• 527681-84-1 methyl 5-O-(2,3-anhydro-5-O-benzoyl-α-D-ribofuranosyl)-2,3-di-O-benzyl-α-D-arabinofuranoside 
• 53458-72-3 methyl 2,3-di-O-benzyl-5-O-p-toluenesulfonyl-α-D-arabinofuranoside 
• 853260-34-1 (2R,3R,4S,5S)-3,4-Bis-benzyloxy-2-ethynyl-5-methoxy-tetrahydro-furan 
• 853260-29-4 (2R,3R,4S,5S)-3,4-Bis-benzyloxy-2-(2,2-dibromo-vinyl)-5-methoxy-tetrahydro-furan 

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.

Preparation method of compound with 3, 4-trans-3, 6-anhydrofuran hexose structure

The invention discloses a preparation method of a compound with a 3, 4-trans-3, 6-dehydrated furan hexose structure and a preparation method of the compound with the 3, 4-trans-3, 6-dehydrated furan hexose structure. The method comprises the following ste

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.

Arabino mycolates from synthetic mycolic acids

The synthesis of single mono-arabino mycolates, important lipid antigens from mycobacteria is described, using structurally defined synthetic mycolic acids. Preliminary assays indicate that these are differentially antigenic to antibodies in the serum of

Neighboring-group participation by C-2 ether functions in glycosylations directed by nitrile solvents

Ether-protecting functions at C-2 hydroxy groups have been found to play participating roles in glycosylations when the reactions are conducted in nitrile solvent mixtures. The participation mechanism is based on intramolecular interaction between the lone electron pair of the oxygen atom of the C-2 ether function and the nitrile molecule when they are positioned in a cis configuration. A 1,2-cis glycosyl oxazolinium intermediate is formed. This participation, in conjunction with the anomeric effect of the glycosyl donor, confers high 1,2-trans selectivities on glycosylations. Further application of this concept has led to efficient preparations of α-(1→5)-arabinan oligomers.

Studies on oxidopyrylium [5 + 2] cycloadditions: Toward a general synthetic route to the C12-hydroxy daphnetoxins

12-Hydroxydaphnetoxins, members of the structurally fascinating daphnane diterpene family, exhibit a wide range of significant biological activities. A general route to the BC-ring system of 12-hydroxy daphnetoxins is reported based on D-ribose. Depending on the choice of protecting groups and solvent, the oxidopyrylium-alkene [5 + 2] cycloaddition originating from A provides cycloadduct diastereomer B or C with good to excellent selectivity.

The new and efficient synthesis of a heptose moiety of spicamycin

The new and efficient synthesis of 7-O-acetyl-4-azido-2,3,6-tri-O-benzyl-4-deoxy-L-glycero-α-L-manno- heptopyranosyl acetate (5), a key intermediate for the synthesis of novel anti-cancer antibiotic, spicamycin (1), starting from D-ribose is described.

Enantiospecific synthesis of the phospholipase A2 inhibitor (-)-cinatrin B

The first enantiospecific synthesis of phospholipase A2 (PLA2) inhibitor (-)-cinatrin B (2) from the D-arabinose derivative 9 is described. The spirolactone system was formed by an Ireland-Claisen rearrangement of the allyl ester 8 followed by hydrolysis and stereoselective iodolactonization. The stereoselectivity of the rearrangement was controlled by the asymmetry in the allylic alcohol fragment. Ester (S)-8 gave the desired rearrangement product 7 and the epimer 13 in high yield as a 73:27 ratio, respectively. The final stereocenter at C2 was introduced via a chelation-controlled addition of the Grignard reagent derived from trimethylsilylacetylene to α-hydroxy ketone 6. Transformation of the terminal alkyne into the methyl ester 21 followed by acetal hydrolysis and selective lactol oxidation afforded cinatrin B methyl ester (22). Base hydrolysis and acid-induced relactonization then gave (-)-cinatrin B (2).

Stereoselective synthesis of 5-methylphosphono-D-arabino hydroximolactone, inhibitor of glucosamine-6-phosphate synthase and phosphoglucose isomerase

Compound 2, synthesized from D-arabinose in 12 steps with an overall 4% yield, is a competitive inhibitor vs fructose-6P for both phosphoglucose isomerase and glucosamine-6P synthase.