62255-44-1

Upstream product

• 160549-10-0 2,3,5-tri-O-benzyl-D-arabinofuranose 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 

Downstream Products

• 148744-13-2 Diphenyl(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)phosphine Oxide 
• 153481-95-9 (2R,3R,4S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-phenylsulfanyl-tetrahydro-furan 
• 70613-79-5 2,3,5-tri-O-benzyl-D-arabinofuranosyl bromide 
• 93041-21-5 1-O-acetyl-2,3-O-bis(phenylmethyl)-α-D-arabinofuranose 
• 4060-34-8 2,3,5-tri-O-benzyl-α-D-arabinofuranosyl chloride 
• 278796-50-2 p-cresyl 2,3,5-tri-O-benzyl-1-thio-D-arabinofuranoside 
• 52554-29-7 2,3,5-tri-O-benzyl-α- and β-D-arabinofuranosyl chlorides 
• 862163-51-7 2'-(benzyloxycarbonyl)benzyl tri-O-benzyl-α-D-arabinofuranoside 
• 38819-10-2 9-β-D-arabinofuranosyl-guanine 
• 35085-24-6 2-amino-6-chloro-9-(2,3,5-triphenylmethoxy-β-D-arabinofuranosyl)purine 
• 85572-58-3 2-Amino-9-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ol 
• 14233-62-6 1,4-anhydro-2,3,5-tri-O-benzyl-D-arabinitol 
• 516482-84-1 benzyl (2S,3R,4R)-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]pyrrolidine-1-carboxylate 
• 516482-80-7 benzyl [(2R,3R,4R)-2,3,5-tris(benzyloxy)-4-hydroxypentyl]carbamate 

Relevant academic research and scientific papers

Diastereoselective Synthesis of α-C-Arabinofuranosyl Glycine

Exploiting N-(tert-butoxycarboxyl)-2-(tert-butyldimethylsiloxy)pyrrole (TBSOP) as a masked glycine anion equivalent, a short enantiospecific synthesis of the title C-glycosyl α-aminoacid 5 was devised and executed, via diastereospecific α-C-glycosylation

Chemoselective and Diastereoselective Synthesis of C-Aryl Nucleoside Analogues by Nickel-Catalyzed Cross-Coupling of Furanosyl Acetates with Aryl Iodides

Canonical nucleosides are vulnerable to enzymatic and chemical degradation, yet their stable mimics—C-aryl nucleosides—have demonstrated potential utility in medicinal chemistry, chemical biology, and synthetic biology, although current synthetic methods remain limited in terms of scope and selectivity. Herein, we report a cross-electrophile coupling to prepare C-aryl nucleoside analogues from readily available furanosyl acetates and aryl iodides. This nickel-catalyzed modular approach is characterized by mild reaction conditions, broad substrate scope, excellent β-selectivity, and high functional-group compatibility. The exclusive chemoselectivity with respect to the aryl iodide enables efficient preparation of a variety of C-aryl halide furanosides suitable for various downstream transformations. The practicality of this transformation is demonstrated through the synthesis of a potent analogue of a naturally occurring NF-κB activator.

Acid catalyzed rearrangement of vinyl and ketene acetals

Substituted vinyl and ketene acetals undergo smooth oxygen-to-carbon rearrangement with a catalytic amount of TMSOTf to afford chain-extended ketones or esters, respectively. The developed procedure has been applied to the stereoselective synthesis of C-glycosides from the corresponding anomeric vinyl ethers.

Stereoselective synthesis of 9-β-d-arabianofuranosyl guanine and 2-amino-9-(β-d-arabianofuranosyl)purine

9-β-d-Arabianofuranosyl guanine (6) and 2-amino-9-(β-d- arabianofuranosyl)purine (8) were prepared from 2-amino-6-chloro-9-(2,3,5- triphenylmethoxyl-β-d-arabianofuranosyl)purine (4), a key intermediate which was stereoselectively prepared from 2,3,5-triphenylmethoxyl-d- arabianofuranose and 2-amino-6-chloro-purine. The yield of the intermediate was obviously improved and only β-isomer was formed by using the activated molecular sieve as environmental friendly catalyst, overcoming the defect that a 1:1 mixture of α- and β-isomers was formed, which was difficult to separate, when toxic mercury cyanide was previously used as catalyst.

Arabinofuranosides from mycobacteria: Synthesis of a highly branched hexasaccharide and related fragments containing β-arabinofuranosyl residues

The synthesis of 11 oligosaccharides (4-14) containing β-arabinofuranosyl residues is reported. The glycans are all fragments of two polysaccharides, arabinogalactan and lipoarabinomannan, which are found in the cell wall complex of mycobacteria. In the preparation of the targets, the key step was a low-]temperature glycosylation reaction that installed the β-arabinofuranosyl residues with good to excellent stereocontrol.

A Glycosylation Protocol Based on Activation of Glycosyl 2-Pyridyl Sulfones with Samarium Triflate

(Equation Presented) Reaction of glycosyl 2-pyridyl sulfones (e.g., 2) with alcohols and samarium(III) triflate affords glycosides in moderate to excellent yields. Benzylated sulfones can be activated in preference to their benzoylated counterparts, and t

The first total synthesis of a highly branched arabinofuranosyl hexasaccharide found at the nonreducing termini of mycobacterial arabinogalactan and lipoarabinomannan

β-D-Araf(1→2)-α-D-Araf |(1→5) α-D-Araf(1→5)-α-D-Araf-OMe |(1→3) β-D-Araf(1→2)-α-D-Araf The first total synthesis of the arabinofuranosyl hexasaccharide present at the nonreducing termini of mycobacterial arabinogalactan and lipoarabinomannan is reported.