52492-40-7

Upstream product

• 31598-80-8 2,3,5-Tri-O-benzyl-1-O-(p-nitrobenzoyl)-β-D-arabinofuranose 
• 160549-10-0 2,3,5-tri-O-benzyl-D-arabinofuranose 
• 62255-44-1 1-O-acetyl-2,3,5-tris-O-(benzyl)-α, β-D-arabinofuranose 

Downstream Products

• 87791-34-2 4-Methylthio-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-1H-pyrrolo<2,3-d>pyrimidin 
• 87791-33-1 4-Methylthio-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin 
• 87791-32-0 4-Methylthio-7-(2,3,5-tri-O-benzyl-α-D-arabinofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin 
• 16754-83-9 7-(β-D-Arabinofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin 
• 87791-35-3 7-(2,3,5-Tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin 
• 90057-11-7 2,4-Dimethoxy-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin 
• 90057-10-6 2,4-Dimethoxy-7-(2,3,5-tri-O-benzyl-α-D-arabinofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin 

Relevant academic research and scientific papers

Synthesis of 1′,2′-cis-Nucleoside analogues: Evidence of stereoelectronic control for SN2 reactions at the anomeric center of furanosides

We are reporting a highly diastereoselective route to 1′,2′- cis-nucleoside analogues in the d-ribo, d-lyxo, d-xylo, and d-arabinoside series. Five-membered ring lactols undergo highly selective N-glycosidation reactions in the presence of dimethylboron bromide with different silylated nucleobases. Stereoelectronic control plays a crucial role for the observed induction, and the products are proposed to be formed through SN2 "exploded" transition states. This approach shows great potential considering its simplicity and selectivity for the synthesis of nucleoside analogues, an important class of molecules in medicinal chemistry.

Stereoselective synthesis of β-arabino glycosyl sulfones as potential inhibitors of mycobacterial cell wall biosynthesis

A series of β-arabino glycosyl sulfones with varying alkyl chain lengths were synthesised in a stereoselective fashion as putative mimics of decaprenolphosphoarabinose (DPA), and as potential inhibitors of mycobacterial cell wall biosynthesis. Biological

ara-7-Deazanebularine - Synthesis of a Fluorescent Pyrrolopyrimidine Nucleoside by Phase-Transfer Glycosylation

ara-7-Deazanebularine (2b) and its 6-methylthio derivative 2a have been synthesized via phase-transfer glycosylation of 4-methylthio-7H-pyrrolopyrimidine (4a) with 1-bromo-2,3,5-tri-O-benzyl-D-arabinofuranose (7).Omitting the halogenose and carrying out the reaction of 4a or 4b in dichloromethane leads to the methylene-bridged chromophores 6a and 6b, respectively.In contrast to pyrrolopyrimidines with substituents in position 2 and 4 compound 4a is glycosylated at N-7 and N-1.The formation of anomers and isomers is influenced by the phase-transfer catalyst.The N-1glycosylated 10 is sensitive against hydrolysis at the N-glycosylic bond which is not found for the N-7 isomer 8a.Debenzylation of the methylthio nucleosides 8a or 9a is accomplished using boron trichloride.Raney nickel catalyst removes the sulfur yielding the title compound 2b which exhibits strong fluorescence.