230631-34-2

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 230631-33-1 1-(3,5-Di-O-benzyl-β-D-allofuranosyl)thymine 
• 124468-96-8 1,2-Isopropylidene-3-O-benzyl-6-O-benzoyl-α-D-allofuranose 
• 1122-58-3 dmap 
• 230631-32-0 1-(2-O-Acetyl-6-O-benzoyl-3,5-di-O-benzyl-β-D-allofuranosyl)thymine 
• 230631-31-9 1,2-Di-O-acetyl-6-O-benzoyl-3,5-di-O-benzyl-D-allofuranose 
• 230631-30-8 6-O-Benzoyl-3,5-di-O-benzyl-1,2-di-O-isopropylidene-α-D-allofuranose 
• 100-39-0 benzyl bromide 

Downstream Products

• 230631-35-3 (1S,4R,5R,7R,8R)-4,8-Dibenzyloxy-7-(thymin-1-yl)-2,6-dioxabicyclo[3.2.1]heptane 

Relevant academic research and scientific papers

XYLO-LNA ANALOGUES

A bicyclic nucleoside derivative, wherein an intranucleoside ring locks the ring conformation of the nucleoside, is termed an LNA - a Locked Nucleic Acid. LNAs of the xylo-configuration, considered useful as therapeutic agents, diagno

Xylo-LNA analogues

Based on the above and on the remarkable properties of the 2′-O,4′-C-methylene bridged LNA monomers it was decided to synthesise oligonucleotides comprising one or more 2′-O,′-C-methylene-β-D-xylofuranosyl nucleotide monomer(s) as the first stereoisomer o

Synthesis and restricted furanose conformations of three novel bicyclic thy mine nucleosides: A xylo-LNA. nucleoside, a 3'-0,5'-Cmethylene-linked nucleoside, and a 2′-0,5′-C-methylene-linked nucleoside

The xylo-LNA nucleoside 1-(2-O,4-C-methylene-β-D-xyIofuranosyl)thymine (9) and the 2′-0,5′-C-methylene linked nucleoside 1-(2,6-anhydro-β-D-altrofuranosyI)thymine (28) were obtained in overall yields of 13% (8 steps) and 31% (7 steps) starting from furanose derivatives 1 and 21, respectively. In the synthesis of 3′-O,5′-C-methylene-linked nucleoside derivatives, cyclization by intramolecular attack from the 6-hydroxy group on the 3-keto functionality to give C-3-hemiketal furanose 11 and its subsequent transformation into nucleoside 15 proved very efficient. It was, however, impossible to isolate the debenzylated 2'-hydroxy, 2'-O-methyl and 2'-O-ter/-butyldimethylsiIyl derivatives 16,18 and 20, respectively, in analytically pure form. Solution-phase conformational analysis showed the bicyclic nucleosides 8,9,14,15,17 and 19 to exist predominantly in an N-type furanose conformation and bicyclic nucleotides 27 and 28 to adopt an S-type conformation.