110415-62-8

Upstream product

• 108-24-7 acetic anhydride 
• 7473-45-2 1-O-methyl-D-ribofuranose 
• 67-56-1 methanol 
• 532-20-7 D-Ribose 
• 1824-96-0 methyl ribofuranoside 
• 36468-53-8 β-D-ribofuranose 
• 10257-32-6 D-ribose 
• 50-69-1 D-ribose 
• 3795-68-4 methyl α-L-arabinofuranoside 
• 532-20-7 D-arabinofuranose 
• 56607-40-0 methyl D-arabinofuranoside 
• 79083-42-4 methyl D-arabinofuranoside 
• 22861-09-2 methyl β-D-arabinofuranoside 
• 22416-73-5 methyl-α-D-lyxofuranoside 

Downstream Products

• 28708-32-9 1,2,3,5-tetra-O-acetyl-D-ribofuranose 
• 52485-92-4 methyl α-D-ribofuranoside 
• 206269-25-2 methyl 2,3,5-tri-O-acetyl-β-L-ribofuranoside 
• 221546-55-0 phenyl 2,3,5-tri-O-acetyl-1-seleno-β-L-xylofuranoside 
• 144490-03-9 1,2,3,5-tetra-O-acetyl-β-L-ribofuranose 
• 659722-55-1 1,2,3,5-tetra-O-acetyl-α-L-ribofuranose 
• 13035-61-5 1,2,3,6-tetra-O-acetyl-5-deoxy-α-L-arabino-hexofuranose 
• 13035-61-5 1,2,3,6-tetra-O-acetyl-5-deoxy-β-L-arabino-hexofuranose 
• 1382683-49-9 2',3'-dideoxy-5-fluoro-5'-O-(tbutyldiphenylsilyl)-α-L-cytidine 
• 13035-61-5 1,2,3,5-tetra-O-acetyl-α-D-arabinofuranose 
• 953089-09-3 Acetic acid (2S,3S,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(6-amino-purin-9-yl)-tetrahydro-furan-3-yl ester 
• 15830-77-0 O²,O³,O⁵-triacetyl-1-(6-amino-purin-9-yl)-β-D-1-deoxy-xylofuranose 
• 77735-42-3 3,4,5-tri-O-acetyl-2-S-benzyl-2-thio-D-lyxose dibenzyl dithioacetal 
• 107271-80-7 9-(2',3',5'-tri-O-acetyl-α-D-lyxofuranosyl)adenine 

Relevant academic research and scientific papers

SELECTIVE DEUTERATION OVER RANEY NICKEL IN DEUTERIUM OXIDE: METHYL GLYCOSIDES

The rate of protium-deuterium exchange, catalyzed by deuterated Raney nickel in deuterium oxide, in various positions in methyl glycopyranosides and furanosides has been studied.In general, the exchange process is not highly regioselective in these compounds.However, conditions were found under which methyl β-D-fructopyranoside can be selectively labelled on C-5, methyl β-D-fructofuranoside on C-3, and methyl β-D-galactopyranoside on C-3 and C-4.

A new process for deprotection of acetyl and benzoyl groups in synthesis of azacitidine

4-Amino-1-β-D-ribofuranosyl-s-triazin-2(1H)-one or azacitidine is a promising DNA demethylation inhibitor used for the treatment of myloneplastic, bone cancer and breast cancer. An efficient, cost-effective and convenient manufacturing process for the synthesis of azacitidine is described. The present research relates to the synthesis, deprotection, isolation and purification of azacitidine (1). In this process, more particularly 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) is used as deprotection reagent for deprotection of O-acetyl, O-benzoyl to acquire azacitidine (1). The new process allows for the reliable and efficient production of drug substance similar overall yield. The new improved process has merits including enantiomeric purity, better crystallization and the product complies with the requirements of USP30.

Synthesis and antiviral evaluation of nucleoside analogues bearing one pyrimidine moiety and two d-ribofuranosyl residues

A series of 1,2,3-triazolyl nucleoside analogues in which 1,2,3-triazol-4-yl-β-D-ribofuranosyl fragments are attached via polymethylene linkers to both nitrogen atoms of the heterocycle moiety (uracil, 6-methyluracil, thymine, quinazoline-2,4-dione, alloxazine) or to the C-5 and N-3 atoms of the 6-methyluracil moiety was synthesized. All compounds synthesized were evaluated for antiviral activity against influenza virus A/PR/8/34/(H1N1) and coxsackievirus B3. Antiviral assays revealed three compounds, 2i, 5i, 11c, which showed moderate activity against influenza virus A H1N1 with IC50 values of 57.5 μM, 24.3 μM, and 29.2 μM, respectively. In the first two nucleoside analogues, 1,2,3-triazol-4-yl-β-D-ribofuranosyl fragments are attached via butylene linkers to N-1 and N-3 atoms of the heterocycle moiety (6-methyluracil and alloxazine, respectively). In nucleoside analogue 11c, two 1,2,3-triazol-4-yl-2′,3′,5′-tri-O-acetyl-β-D-ribofuranose fragments are attached via propylene linkers to the C-5 and N-3 atoms of the 6-methyluracil moiety. Almost all synthesized 1,2,3-triazolyl nucleoside analogues showed no antiviral activity against the coxsackie B3 virus. Two exceptions are 1,2,3-triazolyl nucleoside analogs 2f and 5f, in which 1,2,3-triazol-4-yl-2′,3′,5′-tri-O-acetyl-β-D-ribofuranose fragments are attached to the C-5 and N-3 atoms of the heterocycle moiety (6-methyluracil and alloxazine respectively). These compounds exhibited high antiviral potency against the coxsackie B3 virus with IC50 values of 12.4 and 11.3 μM, respectively, although both were inactive against influenza virus A H1N1. According to theoretical calculations, the antiviral activity of the 1,2,3-triazolyl nucleoside analogues 2i, 5i, and 11c against the H1N1 (A/PR/8/34) influenza virus can be explained by their influence on the functioning of the polymerase acidic protein (PA) of RNA-dependent RNA polymerase (RdRp). As to the antiviral activity of nucleoside analogs 2f and 5f against coxsackievirus B3, it can be explained by their interaction with the coat proteins VP1 and VP2.

Selective monodeacetylation of methyl 2,3,5-tri-O-acetyl-D- arabinofuranoside using biocatalyst

Methyl arabinofuranoside 1 was fully acetylated to methyl 2,3,5-tri-O-acetyl-d-arabinofuranoside 2 and it was regioselectively deacetylated using enzymes. Rhizopus oryzae esterase gave methyl 3,5-di-O-acetyl-d-arabinofuranoside 3, regioselectively. This protected 3 was deoxygenized to 3,5-di-O-acetyl-d-2-deoxyarabinofuranoside 7 using hypophosphorous acid.

Facile exchange of glycosyl S,S-acetals to their O,O-acetals and preparation of glycofuranosides from acyclic glycosyl S,S-acetals under metal-free reaction conditions in the presence of 1,3-dibromo-5,5- dimethylhydantoin

Exchange of acyclic glycosyl dithioacetals to their O,O-acetals has been achieved by a generalized reaction protocol mediated by 1,3-dibromo-5,5- dimethylhydantoin under mild, metal-free and neutral conditions. This methodology has been extended to the sy

Synthesis of the enantiomer of nelarabine

A synthesis of the enantiomer of nelarabine is described. Subtle changes in the protecting group strategy allow for an efficient inversion of the C-2′ stereocentre.

Synthesis of 1,2,3-triazolyl nucleoside analogues and their antiviral activity

Abstract: Based on the fact that a search for influenza antivirals among nucleoside analogues has drawn very little attention of chemists, the present study reports the synthesis of a series of 1,2,3-triazolyl nucleoside analogues in which a pyrimidine fragment is attached to the ribofuranosyl-1,2,3-triazol-4-yl moiety by a polymethylene linker of variable length. Target compounds were prepared by the Cu alkyne-azide cycloaddition (CuAAC) reaction. Derivatives of uracil, 6-methyluracil, 3,6-dimethyluracil, thymine and quinazolin-2,4-dione with ω-alkyne substituent at the N1 (or N5) atom and azido 2,3,5-tri-O-acetyl-D-β-ribofuranoside were used as components of the CuAAC reaction. All compounds synthesized were evaluated for antiviral activity against influenza virus A/PR/8/34/(H1N1) and coxsackievirus B3. The best values of IC50 (inhibiting concentration) and SI (selectivity index) were demonstrated by the lead compound 4i in which the 1,2,3-triazolylribofuranosyl fragment is attached to the N1 atom of the quinazoline-2,4-dione moiety via a butylene linker (IC50 = 30?μM, SI = 24) and compound 8n in which the 1,2,3-triazolylribofuranosyl fragment is attached directly to the N5 atom of the 6-methyluracil moiety (IC50 = 15?μM, SI = 5). According to theoretical calculations, the antiviral activity of the 1,2,3-triazolyl nucleoside analogues 4i and 8n against H1N1 (A/PR/8/34) influenza virus can be explained by their influence on the functioning of the polymerase acidic protein (PA) of RNA-dependent RNA polymerase (RdRP). Graphic abstract: [Figure not available: see fulltext.]

A stereoselective synthesis method for β-D-arabinofuran glycoside bonds

The present invention belongs to the field of natural oligosaccharide chain synthesis technology, specifically relates to a β-D- arabinofuran glycoside bond stereoselective synthesis method, the present invention to 2- O- benzyl-3,5-O- xylene -D- arabfura

Highly Stereoselective Glycosylation Reactions of Furanoside Derivatives via Rhenium (V) Catalysis

A novel approach for the formation of anomeric carbon-functionalized furanoside systems was accomplished through the employment of an oxo-rhenium catalyst. The transformation boasts a broad range of nucleophiles including allylsilanes, enol ethers, and aromatics in addition to sulfur, nitrogen, and hydride donors, able to react with an oxocarbenium ion intermediate derived from furanosidic structures. The excellent stereoselectivities observed followed the Woerpel model, ultimately providing 1,3-cis-1,4-trans systems. In the case of electron-rich aromatic nucleophiles, an equilibration occurs at the anomeric center with the selective formation of 1,3-trans-1,4-cis systems. This anomalous result was rationalized through density functional theory calculations. Different oxocarbenium ions such as those derived from dihydroisobenzofuran, pyrrolidine, and oxazolidine heterocycles can also be used as a substrate for the oxo-Re-mediated allylation reaction.

A Concise Synthesis of Oligosaccharides Derived From Lipoarabinomannan (LAM) with Glycosyl Donors Having a Nonparticipating Group at C2

Mycobacteria infection resulting in tuberculosis (TB) is one of the top ten leading causes of death over the world, and lipoarabinomannan (LAM) has been confirmed to play significant roles in this process. In this study, a convenient synthetic approach ha