70831-62-8

Basic information

• Product Name: methyl 2,3-di-O-benzyl-β-D-ribofuranoside
• Synonyms: methyl 2,3-di-O-benzyl-β-D-ribofuranoside
• CAS NO: 70831-62-8
• Molecular Weight: 344.408
• Mol File: 70831-62-8.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: methyl 2,3-di-O-benzyl-β-D-ribofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3-di-O-benzyl-β-D-ribofuranoside(70831-62-8)
• EPA Substance Registry System: methyl 2,3-di-O-benzyl-β-D-ribofuranoside(70831-62-8)

Safety Data

• Hazardous Substances Data: 70831-62-8(Hazardous Substances Data)

Upstream product

• 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 
• 532-20-7 D-Ribose 
• 1824-96-0 methyl ribofuranoside 
• 1251531-61-9 Methyl 2,3 di-O-benzyl-5-O-trityl-D-ribofuranoside 
• 532401-39-1 methyl 2,3-di-O-benzyl-α-D-ribofuranoside 
• 56607-40-0 methyl D-arabinofuranoside 
• 1360561-10-9 C₃₆H₄₂O₅Si 
• 79083-42-4 methyl D-arabinofuranoside 
• 10323-20-3 D-Arabinose 
• 4060-35-9 methyl 5-O-trityl-α-D-arabinofuranoside 
• 4119-19-1 Methyl-(2,3-di-O-benzyl-5-O-trityl-α-L-arabinofuranosid) 

Downstream Products

• 697298-48-9 methyl 2,3-di-O-benzyl-5-dehydro-α-D-arabinofuranoside 
• 482631-88-9 (2S,3S,4R,5R)-3,4-Bis-benzyloxy-2-iodomethyl-5-methoxy-tetrahydro-furan 
• 404935-58-6 (2S,3S,4S,5S)-3,4-Bis-benzyloxy-5-methoxy-tetrahydro-furan-2-carboxylic acid 
• 404935-57-5 (2S,3S,4S,5S)-3,4-Bis-benzyloxy-5-methoxy-tetrahydro-furan-2-carboxylic acid 1-vinyl-decyl ester 
• 404935-68-8 (2S,3S,4S,5S)-3,4-Bis-benzyloxy-5-methoxy-tetrahydro-furan-2-carboxylic acid (S)-1-vinyl-decyl ester 
• 404935-69-9 (2S,3S,4S,5S)-3,4-Bis-benzyloxy-5-methoxy-tetrahydro-furan-2-carboxylic acid (R)-1-vinyl-decyl ester 
• 1320337-26-5 methyl 5-O-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-2,3-di-O-benzyl-α-D-arabinofuranoside 
• 1360560-53-7 methyl 2,3-di-O-benzyl-5-O-(tert-butyldiphenylsilyl)-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzyl-α-D-arabinofuranoside 
• 402758-98-9 methyl 2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzyl-α-D-arabinofuranoside 
• 492470-84-5 1-((2R,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-2-((2R,3R,4S,5S)-3,4-bis-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-2-nitro-ethanol 
• 492470-85-6 (2S,3S,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-nitromethyl-tetrahydro-furan 
• 532401-52-8 (R)-1-((2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-isopropoxy-3-methoxymethoxy-tetrahydro-pyran-2-yl)-ethane-1,2-diol 

Relevant articles and documents

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.

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.