55781-64-1

Upstream product

• 16162-35-9 1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-xylofuranose 
• 532-20-7 D-xylofuranose 
• 1824-96-0 methyl xylofuranoside 
• 120964-98-9 methyl 2,3,5-tri-O-benzoyl-αβ-D-xylbofuranoside 
• 98-88-4 benzoyl chloride 

Downstream Products

• 113575-01-2 3,5-di-O-benzoyl-1,2--α-D-ribofuranose 
• 113575-02-3 1,2--α-D-ribofuranose 

Relevant academic research and scientific papers

Gold(III)-catalyzed glycosidations for 1,2- trans and 1,2- cis furanosides

Stereoselective synthesis of furanosides is still a daunting task, unlike the pyranosides, for which several methods exist. Herein, a unified stereoselective strategy for the synthesis of 1,2-trans and 1,2-cis furanosides is revealed for seven out of eight possible isomers of pentoses. The identified protocol gives access to diastereoselective synthesis of α- and β-araf, ribf, lyxf, and α-xylf furanosides. 1,2-trans glycosides were synthesized by the use of propargyl 1,2-orthoesters under gold-catalyzed glycosidation conditions, and subsequently, they are converted into 1,2-cis glycosides through oxidation-reduction as the key functional group transformation. All the reactions are found to be fully diastereoselective, mild, and high yielding.

Ready preparation of furanosyl n-pentenyl orthoesters from corresponding methyl furanosides

The 3,5-di-O-benzoyl n-pentenyl orthoesters of the four pentofuranoses have been prepared. The first key intermediate in each case is the methyl pentofuranoside(s), and a user-friendly procedure for the preparation of each, based on the Callam-Lowary precedent, is described, whereby formation of the crucial α/β anomeric mixture is optimized. The mixture is used directly to prepare the corresponding perbenzoylated pentofuranosyl bromide(s) and then the title compounds.

An Efficient Route to Pyrimidine Nucleoside Analogues by [4 + 2] Cycloaddition Reaction

We report here an efficient synthesis for pyrimidine nucleoside analogues by [4 + 2] cycloaddition reaction. These compounds were obtained by convergent chemistry from glycosyl isothiocyanates 3a-f (pyranoses, furanoses, and dissaccharides) and diazadienium salt 5. In fact, diazapentadienium iodide 5 prepared from vinylthioamide 4 is an efficient intermediate in heterocyclic synthesis and reacts with isothiocyanates 3a-f affording β-D-uracil analogues 7a-f in good yields and with total regiocontrol. All compounds were fully characterized by IR, HRMS, and 13C and 1H NMR (COSY and HMQC).