904893-24-9

Upstream product

• 16838-89-4 2,3,5-tri-O-benzyl-D-xylofuranose 
• 1225026-99-2 C₂₈H₃₃NO₇S 
• 1392126-44-1 (-)-(2R,3R,4R)-1,3,4-tris(benzyloxy)-5,5-bis(ethylthio)pentan-2-yl methanesulfonate 
• 201290-06-4 3,4,6-tri-O-benzyl-1,2-dideoxy-D-xylo-hex-1-enitol 
• 904893-23-8 (3S,4R,5R)-5-methanesulfonyloxy-3,4,6-tribenzyloxy-1-hexene 

Downstream Products

• 904893-22-7 (2S,3S,4S)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro-2H-pyrrole-1-oxide 
• 151265-55-3 (2S,3S,4S,5S)-2-hydroxymethyl-5-phenylpyrrolidine-3,4-diol 
• 904893-25-0 (2S,3S,4S,5S)-2-benzyloxymethyl-3,4-dibenzyloxy-5-phenyl-N-hydroxy-pyrrolidine 
• 904893-28-3 (2S,3S,4S,5S)-2-benzyloxymethyl-3,4-dibenzyloxy-5-(4-benzyloxyphenyl)-N-hydroxy-pyrrolidine 
• 904893-27-2 (2S,3S,4S,5S)-2-benzyloxymethyl-3,4-dibenzyloxy-5-(3-benzyloxy-4-methoxyphenyl)-N-hydroxy-pyrrolidine 
• 905286-72-8 (2S,3S,4S,5S)-2-hydroxymethyl-3,4-dihydroxy-5-(4-hydroxyphenyl)-pyrrolidine 
• 905286-71-7 (2S,3S,4S,5S)-2-hydroxymethyl-3,4-dihydroxy-5-(3-hydroxy-4-methoxyphenyl)-pyrrolidine 
• 1392126-75-8 (+)-1-((2R,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione 
• 171721-08-7 (-)-1-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 
• 1392126-51-0 (-)-(2R,3R,4R,5S)-1,3,4-tris(benzyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((trimethylsilyl)oxy)pentan-2-yl methanesulfonate 
• 1392126-57-6 (-)-(2R,3R,4R,5S)-1,3,4-tris(benzyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((trimethylsilyl)oxy)pentan-2-yl methanesulfonate 
• 1392126-62-3 (-)-(2R,3R,4R,5S)-5-(6-Amino-9H-purin-9-yl)-1,3,4-tris(benzyloxy)-5-((trimethylsilyl)oxy)pentan-2-yl methanesulfonate 
• 171721-10-1 (-)-9-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)-9H-purin-6-amine 
• 1392126-66-7 (-)-(2R,3R,4R,5S)-1,3,4-tris(benzyloxy)-5-(5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((trimethylsilyl)oxy)pentan-2-yl methanesulfonate 

Relevant academic research and scientific papers

A stereoselective approach to β-L-arabino nucleoside analogues: Synthesis and cyclization of acyclic 1′,2′-syn N, O-Acetals

Reported herein is a novel and versatile strategy for the stereoselective synthesis of unnatural β-l-arabinofuranosyl nucleoside analogues from acyclic N,OTMS-acetals bearing pyrimidine and purine bases. These unusual acetals undergo a C1′ to C4′ cyclization where the OTMS of the acetal serves as the nucleophile to generate 2′-oxynucleosides with complete retention of configuration at the C1′ acetal center. N,OTMS-acetals are obtained diastereoselectively from additions of silylated nucleobases onto acyclic polyalkoxyaldehydes in the presence of MgBr 2·OEt2. The strategy reported is addressing important synthetic challenges by providing stereoselective access to unnatural l-nucleosides starting from easily accessible pools of d-sugars and, as importantly, by allowing the formation of the sterically challenging 1′,2′-cis nucleosides. A wide variety of nucleoside analogues were synthesized in 7-8 steps from easily accessible d-xylose.

A practical synthesis of sugar-derived cyclic nitrones: Powerful synthons for the synthesis of iminosugars

Sugar-derived cyclic nitrones were synthesized from the corresponding aldoses through an efficient and practical procedure involving a seven-step reaction sequence in good to excellent overall yield (10-42%). This synthetic strategy, requiring only inexpe

Radicamines A and B: Synthesis and revision of the absolute configuration

Starting from D-xylose, enantioselective syntheses of 1 and 2, the proposed structures for radicamines A and B, were accomplished. Both 1H and 13C NMR spectra of 1 and 2 were identical with those of the natural products, but the optical rotation measurements identified that 1 and 2 were actually the enantiomers of the natural radicamines A and B, respectively.