206269-25-2

Upstream product

• 52689-56-2 methyl β-L-ribofuranoside 
• 108-24-7 acetic anhydride 
• 67-56-1 methanol 
• 41546-19-4 α-L-lyxose 
• 24259-59-4 L-ribose 
• 75-36-5 acetyl chloride 
• 110415-62-8 methyl 2,3,5-tri-O-acetyl-α-L-ribofuranoside 
• 390824-25-6 1,5-di-O-acetyl-3-O-benzyl-2-O-methanesulfonyl-L-arabinofuranose 
• 390824-26-7 methyl 3-O-benzyl-β-L-ribofuranoside 

Downstream Products

• 144490-03-9 1,2,3,5-tetra-O-acetyl-β-L-ribofuranose 
• 110415-62-8 methyl 2,3,5-tri-O-acetyl-α-L-ribofuranoside 
• 390824-35-8 N²-acetyl-9-(2',3',5'-tri-O-acetyl-β-L-ribofuranosyl)-6-O-diphenylcarbamoylguanine 
• 390824-34-7 9-(2',3',5'-tri-O-acetyl-β-L-ribofuranosyl)-6-N-benzoyladenine 
• 58-61-7 L-adenosine 
• 659722-55-1 1,2,3,5-tetra-O-acetyl-α-L-ribofuranose 

Relevant academic research and scientific papers

Reaction kinetics and mechanism of sulfuric acid-catalyzed acetolysis of acylated methyl l-ribofuranosides

The mechanism of the sulfuric acid-catalyzed acetolysis of methyl 2,3,5-tri-O-acetyl- and methyl 2,3,5-tri-O-benzoyl-Lribofuranosides and the accompanying anomerization of both the starting material and the 1,2,3,5-tetra-O-acetyl- and 1-O-acetyl-2,3,5-tri-O-benzoyl-L-ribofuranoses formed was investigated. The progress of the reactions was followed by 1H NMR spectroscopy and the rate constants for the reactions were determined for a proposed kinetic model. The role of H+ and Ac + as the catalytically active species was clarified, proving that the anomerization of the acylated methyl furanosides is activated by protonation, while, on the contrary, the anomerization of the 1-O-acetyl ribofuranoses is activated by the acetyl cation. The anomerization of the acylated methyl furanosides was verified to be activated on the ring oxygen leading to endocyclic CO-bond rupture while the 1O-acetyl ribofuranoses are activated on the acetyloxy group on C(1) leading to exocyclic cleavage.

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.

Monocyclic L-nucleosides, analogs and uses thereof

Novel monocyclic L- nucleoside compounds have general formula (I). Embodiments of these compounds are contemplated to be useful in treating a wide variety of diseases including infections, infestations, neoplasms, and autoimmune diseases. Viewed in terms of mechanism, embodiments of the novel compounds show immunomodulatory activity, and are expected to be useful in modulating the cytokine pattern, including modulation of Th 1 and Th 2 response.

A stereospecific synthesis of L-deoxyribose, L-ribose and L-ribosides

Using an inexpensive D-galactose from the chiral pool, L-deoxyribose, L-ribose and their derivatives were synthesized via mild reaction conditions. During the synthesis of L-deoxyribose, the key deoxygenation of the 2-hydroxy group of 3,5-O-dibenzyl-methyl-L-arabinofuranoside was performed by reduction of the corresponding triflate with tetrabutylammonium borohydride in high yield. During the synthesis of L-ribose, the key step of inversion of the 2-hydroxy group in the same substrate was carried out by intramolecular SN2 tandem reaction. Then the L-ribosyl donors were submitted to glycosidations according to Vorbrüggen's conditions to give L-ribosides (L-uridine, L-5-fluorouridine, L-iodouridine, L-thymidine, L-puridine, L-adenosine and L-guanosine) in excellent yields.

Monocyclic L-Nucleosides, analogs and uses thereof

Novel monocyclic L-Nucleoside compounds have the general formula STR1 Embodiments of these compounds are contemplated to be useful in treating a wide variety of diseases including infections, infestations, neoplasms, and autoimmune diseases. Viewed in terms of mechanism, embodiments of the novel compounds show immunomodulatory activity, and are expected to be useful in modulating the cytokine pattern, including modulation of Th1 and Th2 response.