390824-30-3

Upstream product

• 65-71-4 thymin 
• 390824-28-9 1,2,5-tri-O-acetyl-3-O-benzyl-β-L-ribofuranose 
• 390824-26-7 methyl 3-O-benzyl-β-L-ribofuranoside 
• 390824-27-8 methyl 2,5-di-O-acetyl-3-O-benzyl-β-L-ribofuranoside 
• 390824-25-6 1,5-di-O-acetyl-3-O-benzyl-2-O-methanesulfonyl-L-arabinofuranose 
• 390824-24-5 methyl 3,5-di-O-benzyl-2-O-methanesulfonyl-L-arabinofuranoside 
• 190583-85-8 1,2-O-isopropylidene-3,5-di-O-benzyl-β-L-arabinofuranose 

Downstream Products

• 26879-47-0 1-(β-L-ribofuranosyl)thymine 
• 446251-77-0 1-(3'-O-benzyl-β-L-ribofuranosyl)thymine 

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.

A stereospecific synthesis of L-ribose and L-ribosides from D-galactose

An inexpensive D-galactose was converted into L-ribose and its derivatives via mild reaction conditions. The L-ribosyl donor was submitted to a glycosidation according to Vorbrüggen's conditions to give L-ribosides in high yields.