58214-53-2

Usage

Chemical composition

A ribofuranose sugar molecule with three benzoate groups attached to it.

Usage

Often used as a building block in the synthesis of nucleoside analogs and other bioactive molecules.

Versatility

Structure and properties make it a versatile intermediate for the preparation of various pharmaceuticals and biologically active compounds.

Stability

Benzoate groups on the ribofuranose molecule provide stability.

Modifiability

Benzoate groups can be further modified to tailor the compound's reactivity and specificity for different applications.

Importance

Plays a crucial role in organic synthesis and drug discovery.

Upstream product

• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 50909-47-2 2,3,5-tri-O-benzoyl-α-D-ribofuranosyl chloride 
• 333-20-0 potassium thioacyanate 
• 16205-60-0 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl bromide 
• 5991-01-5 2,3,5-(tri-O-benzoyl)-D-ribofuranosyl chloride 
• 22860-91-9 2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide 

Downstream Products

• 77049-63-9 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-S-methylisothiobiuret 
• 79715-31-4 C₂₉H₂₅N₃O₇S₂ 
• 77049-75-3 C₂₈H₂₃N₃O₈S₂ 
• 77049-78-6 C₂₉H₂₅N₃O₈S₂ 
• 79857-63-9 C₃₄H₂₇N₃O₇S 
• 77049-72-0 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-methylsulfanyl-1,3,5-triazine-2(1H)-thione 
• 81742-99-6 1-(2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl)imidazol-2-thion 
• 385433-37-4 (S)-1-[4-(methoxycarbonyl)benzyl]-2-(2',3',5'-tribenzoyl-β-D-ribofuranosyl)amino-4-phenyl-4,5-dihydro-6-pyrimidinone 
• 627812-08-2 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-methylsulfanyl-1,2-dihydropyrimidin-2-thione 
• 79857-57-1 C₂₉H₂₇N₃O₈S 

Relevant academic research and scientific papers

A novel, simple cyclocondensation reaction towards glycosyl triazines

Sugars bearing an isothiocyanate moiety at C-1 react with diazadienium iodide to afford glycosyl triazines that represent, through an easy cyclocondensation reaction step, a flexible entry to different nucleoside analogues. We herein demonstrate that this [4+2] cycloaddition reaction occurs with total regiocontrol and good yields. Subsequent transformation of the thiocarbonyl into a carbonyl, and nucleophilic substitution of the methylsulfanyl group by ammonia, yields the 5-azacytidine analogues. All compounds were fully characterised by IR, HRMS, and 13C and 1H NMR (COSY, HMBC and HMQC). Georg Thieme Verlag.

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).

Facile synthesis of glycofuranosyl isothiocyanates

Peracylated glycofuranosyl isothiocyanates are obtained under smooth conditions starting from the corresponding glycosyl chloride by reaction with potassium thiocyanate in anhydrous acetone at room temperature, classical conditions for the synthesis of gl

STUDIES ON NUCLEOSIDE ANALOGS. XXIV. MONO- AND DISACCHARIDE ISOTHIOCYANATES

The reaction of mono- and disaccharide bromide with Pb(SCN)2 or AgSCN in dry benzene or benzene-toluene gives the respective mono- and disaccharide isothiocyanates and the confirmation of their stereochemistry of mono- and disaccharide isothiocyanates is