58214-53-2

Basic information

• Product Name: 2 3 5-TRI-O-BENZOYL-BETA-D-RIBOFURANOSYL
• Synonyms: 2 3 5-TRI-O-BENZOYL-BETA-D-RIBOFURANOSYL;2,3,5-tri-o-benzoyl-β-d-ribofuranosyl isothiocyanate;β-d-ribofuranosyl isothiocyanate tribenzoate;2,3,5-Tri-O-benzoyl-b-D-ribofuranosyl isothiocyanate
• CAS NO: 58214-53-2
• Molecular Formula: C₂₇H₂₁NO₇S
• Molecular Weight: 503.53
• Mol File: 58214-53-2.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• BRN: 1275438
• CAS DataBase Reference: 2 3 5-TRI-O-BENZOYL-BETA-D-RIBOFURANOSYL(CAS DataBase Reference)
• NIST Chemistry Reference: 2 3 5-TRI-O-BENZOYL-BETA-D-RIBOFURANOSYL(58214-53-2)
• EPA Substance Registry System: 2 3 5-TRI-O-BENZOYL-BETA-D-RIBOFURANOSYL(58214-53-2)

Safety Data

• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 58214-53-2(Hazardous Substances Data)

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

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

Downstream Products

• 79857-57-1 C₂₉H₂₇N₃O₈S 
• 385433-37-4 (S)-1-[4-(methoxycarbonyl)benzyl]-2-(2',3',5'-tribenzoyl-β-D-ribofuranosyl)amino-4-phenyl-4,5-dihydro-6-pyrimidinone 
• 77049-72-0 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-methylsulfanyl-1,3,5-triazine-2(1H)-thione 
• 79857-63-9 C₃₄H₂₇N₃O₇S 
• 77049-78-6 C₂₉H₂₅N₃O₈S₂ 
• 77049-75-3 C₂₈H₂₃N₃O₈S₂ 
• 79715-31-4 C₂₉H₂₅N₃O₇S₂ 
• 81742-99-6 1-(2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl)imidazol-2-thion 
• 627812-08-2 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-methylsulfanyl-1,2-dihydropyrimidin-2-thione 
• 81742-98-5 C₃₃H₃₆N₂O₉S 

Relevant articles and documents

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.

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