13039-64-0

Basic information

• Product Name: (2S,3R,4R)-2-(hydroxymethyl)-5-methoxytetrahydrofuran-3,4-diol
• Synonyms: (2S,3R,4R)-2-(hydroxymethyl)-5-methoxytetrahydrofuran-3,4-diol
• CAS NO: 13039-64-0
• Molecular Weight: 164.158
• Mol File: 13039-64-0.mol
• Article Data: 83

Chemical Properties

• CAS DataBase Reference: (2S,3R,4R)-2-(hydroxymethyl)-5-methoxytetrahydrofuran-3,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,4R)-2-(hydroxymethyl)-5-methoxytetrahydrofuran-3,4-diol(13039-64-0)
• EPA Substance Registry System: (2S,3R,4R)-2-(hydroxymethyl)-5-methoxytetrahydrofuran-3,4-diol(13039-64-0)

Safety Data

• Hazardous Substances Data: 13039-64-0(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 1114-34-7 D-lyxose 
• 50-69-1 D-ribose 
• 58-86-6 D-xylose 
• 609-06-3 L-xylose 
• 5328-37-0 L-arabinose 
• 532-20-7 D-xylofuranose 
• 75-36-5 acetyl chloride 
• 87-72-9 D-Xylose 
• 36468-53-8 β-D-ribofuranose 
• 63846-98-0 1,2-O-(1-Methylethylidene)-α-D-ribo-pentodialdo-1,4-furanose 
• 4495-04-9 1,2-O-isopropylidene-α-D-allofuranose 
• 2595-05-3 Diacetone D-glucose 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 

Downstream Products

• 52783-53-6 methyl 2,3,3'-tri-O-benzoyl-β-D-apiofuranoside 
• 52783-87-6 methyl 2,3,5-tri-O-benzoyl-α-D-ribofuranoside 
• 69350-76-1 methyl 2,3,5-tri-O-benzoyl-αβ-D-ribofuranoside 
• 874770-89-5 [6-methoxy-2-(4-methoxyphenyl)tetrahydrofuro[3,4-d][1,3]-dioxol-4-yl]methanol 
• 14233-62-6 2,3,5-tri-O-benzyl-1-deoxy-D-ribofuranose 
• 160308-10-1 1,4-anhydro-5-O-benzoyl-2-deoxy-2-<3,4-dihydro-2,4-dioxo-5-methyl-1(2H)-pyrimidinyl>-D-lyxitol 
• 149125-44-0 Benzoic acid (2R,3R,4R)-3-methanesulfonyloxy-4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 
• 140623-93-4 1,4-anhydro-2-deoxy-2-<3,4-dihydro-2,4-dioxo-5-methyl-1(2H)-pyrimidinyl>-D-arabinitol 
• 160308-12-3 5-O-benzoyl-2-deoxy-1,4-O²,3-anhydro-2-<3,4-dihydro-4-oxo-1(2H)-pyrimidinyl>-D-lyxitol 
• 259137-72-9 Benzoic acid (2R,3S,4R)-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester 
• 160308-13-4 1,4-anhydro-5-O-benzoyl-2-deoxy-2-<3,4-dihydro-4-oxo-1(2H)-pyrimidinyl>-D-lyxitol 
• 491-19-0 1,4-anhydro-D-ribitol 
• 4099-85-8 methyl 2,3-O-isopropylidene-D-ribofuranoside 
• 303041-42-1 methyl 2,3,5-tri-O-[3-(trifluoromethyl)benzoyl]-D-ribofuranoside 

Relevant articles and documents

MODIFIED OLIGOMERIC COMPOUNDS AND USES THEREOF

The present disclosure provides oligomeric compounds comprising a modified oligonucleotide having at least one stereo-non-standard nucleoside. An oligomeric compound comprising a modified oligonucleotide consisting of 12-30 linked nucleosides, wherein at least one nucleoside of the modified oligonucleotide is a stereo-non-standard nucleoside; and wherein the oligomeric compound is selected from among an RNAi compound, a modified CRISPR compound, and an artificial mRNA compound.

Stereoselective Synthesis of Ribofuranoid exo-Glycals by One-Pot Julia Olefination Using Ribofuranosyl Sulfones

One-pot Julia olefination using ribofuranosyl sulfones is described. The α-anomers of the ribofuranosyl sulfones were synthesized with complete α-selectivity via the glycosylation of heteroarylthiols using ribofuranosyl iodides as glycosyl donors and the subsequent oxidation of the resulting heteroaryl 1-thioribofuranosides with magnesium monoperphthalate (MMPP). The Julia olefination of the α-ribofuranosyl sulfones with aldehydes proceeded smoothly in one pot to afford the thermodynamically less stable (E)-exo-glycals with modest-to-excellent stereoselectivity (up to E/Z = 94:6) under the optimized conditions. The E selectivity was especially high for aromatic aldehydes. In contrast, the (Z)-exo-glycal was obtained as the main product with low stereoselectivity when the corresponding β-ribofuranosyl sulfone was used (E/Z = 41:59). The remarkable impact of the anomeric configuration of the ribofuranosyl sulfones on the stereoselectivity of the Julia olefination has been rationalized using density functional theory (DFT) calculations. The protected ribose moiety of the resulting exo-glycals induced completely α-selective cyclopropanation on the exocyclic carbon-carbon double bond via the Simmons-Smith-Furukawa reaction. The 2-cyanoethyl group was found to be useful for the protection of the exo-glycals, as it could be removed without affecting the exocyclic C=C bond.

ANTIVIRAL NUCLEOSIDES AND DERIVATIVES THEREOF

Disclosed herein are nucleoside compounds and derivatives thereof, pharmaceutical compositions containing same, and their methods of synthesis. The compounds are useful in treating orthomyxovirus infections, such as influenza infections.