659722-55-1

Upstream product

• 108-24-7 acetic anhydride 
• 206269-25-2 methyl 2,3,5-tri-O-acetyl-β-L-ribofuranoside 
• 176299-71-1 1,2,3,5-tetraacetyl-L-ribofuranose 
• 64-19-7 acetic acid 
• 659722-56-2 methyl 2,3,5-tri-O-acetyl-β/α-L-ribofuranoside 
• 162491-62-5 (2S,3R,4S)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol 

Downstream Products

• 144490-03-9 1,2,3,5-tetra-O-acetyl-β-L-ribofuranose 

Relevant academic research and scientific papers

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.

METHOD FOR PRODUCTION OF FURANOSE DERIVATIVE

An object of the present invention is to provide a industrially appropriate method for producing the β-anomers of ribofuranose derivatives in a highly selective manner at a high yield. The present invention provides a method for producing ribofuranose derivatives wherein β-anomers is precipitated from among the generated furanose derivatives by controlling the amount of a reaction reagent used and/or using a poor solvent in the acetolysis reactions of 2,3,5-tri-O-acyl-1-O-alkyl-ribofuranose and 2,3-di-O-acyl-1-O-alkyl-5-deoxy-ribofuranose.

Synthesis of methyl 1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-1,2,4- triazole-3-carboxylate from L-ribose: From a laboratory procedure to a manufacturing process

A two-step manufacturing process for methyl 1-(2,3,5-tri-O-acetyl-β-L- ribofuranosyl)-1,2,4-triazole-3-carboxylate (1) was developed. In step 1, L-ribose was converted to a β/α mixture of 1,2,3,5-tetra-O-acetyl-L- ribofuranoses (2 and 4). The step contained four chemical transformations and was completed in "one-pot" in approximately 95% yield. The crude step 1 product was reacted with methyl 1,2,4-triazole-3-carboxylate (3) in step 2 to produce 1. The successful utilization of both isomers (2 and 4) in step 2 offered advantages of higher overall yield and a much simplified process by eliminating the isolation of pure 2. The process was successfully scaled up to the pilot plant and subsequently in a manufacturing campaign using commercial production facilities.

Process for producing a ribofuranose

A method of converting pure α-anomer or β/α-anomer mixtures of 1,2,3,5-tetra-O-acetyl-L-ribofuranose to methyl-1-(2,3,5 -tri-O-acetyl-β-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate an intermediate for levovirin, as well as, the novel pure α-anomer, alpha 1,2,3,5-tetra-O-acetyl-L-ribofuiranose, are useful in manufacturing levovirin.