22224-38-0

Basic information

• Product Name: 1,2,3,5-tetra-O-benzoyl-β-D-ribofuranose
• Synonyms: 1,2,3,5-tetra-O-benzoyl-β-D-ribofuranose
• CAS NO: 22224-38-0
• Molecular Weight: 566.564
• Mol File: 22224-38-0.mol

Chemical Properties

• CAS DataBase Reference: 1,2,3,5-tetra-O-benzoyl-β-D-ribofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,5-tetra-O-benzoyl-β-D-ribofuranose(22224-38-0)
• EPA Substance Registry System: 1,2,3,5-tetra-O-benzoyl-β-D-ribofuranose(22224-38-0)

Safety Data

• Hazardous Substances Data: 22224-38-0(Hazardous Substances Data)

Upstream product

• 110-86-1 pyridine 
• 50-69-1 D-ribose 
• 98-88-4 benzoyl chloride 
• 102019-31-8 O¹,O⁵-Dibenzoyl-β-D-ribofuranose 
• 55797-81-4 O²,O³,O⁵-Tribenzoyl-D-ribose 
• 115385-43-8 O¹,O²,O⁵-Tribenzoyl-β-D-ribofuranose 
• 109917-97-7 2,3,5-tri-O-benzoyl-1-O-trifluoroacetyl-α,β-D-ribofuranose 
• 65-85-0 benzoic acid 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 54946-48-4 benzyl-β-D-ribofuranoside 
• 98796-65-7 O¹,O³,O⁵-Tribenzoyl-β-D-ribofuranose 
• 5991-01-5 2,3,5-(tri-O-benzoyl)-D-ribofuranosyl chloride 
• 532-31-0 silver benzoate 

Downstream Products

• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 115459-50-2 2,3,5-Tri-O-benzoyl-D-ribofuranose 
• 169687-74-5 N⁶-benzoyl-9-[3,5-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]adenine 
• 855006-73-4 4,7-difluoro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-imidazo[4,5-c]pyridine 
• 1613530-27-0 C₃₄H₂₉N₅O₈ 
• 1613530-28-1 C₃₂H₂₉N₃O₈ 
• 1613530-29-2 C₃₃H₂₇N₅O₉ 
• 1613530-30-5 C₃₁H₂₇N₃O₉ 
• 25692-02-8 2',3',5'-tri-O-benzoyl-5-ethyluridine 
• 37805-86-0 5-methoxyuridine 2',3',5'-tri-O-benzoate 
• 94619-73-5 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4,5-dicyanoimidazole 
• 5991-01-5 2,3,5-(tri-O-benzoyl)-D-ribofuranosyl chloride 
• 329188-20-7 N⁶-benzoyl-9-[3,5-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(β-D-ribofuranosyl)-β-D-ribofuranosyl]adenine 
• 862973-70-4 1-((2R,3R,4R,5R)-3,4-Bis-benzoyloxy-5-benzoyloxymethyl-tetrahydro-furan-2-yl)-5-(cyano-fluoro-methyl)-1H-imidazole-4-carboxylic acid methyl ester 

Relevant articles and documents

Synthesis of novel 6-substituted thymine ribonucleosides and their 3′-fluorinated analogues

Nine novel 6-fluorothymine nucleoside analogues of both N(1)-α/β and N(3)-β-ribo series were prepared by the Vorbrüggen method starting from persilylated 6-fluorothymine and 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose, 1-O-acetyl-2,5-di-O-benzoyl-3-deoxy-3-fluoro-α,β-D-ribofuranose or 1,2,3,5-tetra-O-benzoyl-β-D-ribofuranose and its α-anomer. Protected N(3)-β-D-ribofuranosides were prepared as sole products in high yields at room temperature. A mixture of benzoylated N(1)-β- and α-anomeric ribonucleosides was obtained at lower temperatures. Yields of β-anomers and stereoselectivities (β:α=2.2/4.5:1) of the condensation reactions depended on reaction conditions and the structure of the glycosylating agent. Debenzoylation of 6-fluorothymine N(1)- or N(3)-β-D-ribofuranosides and their 3′-fluorodeoxy analogues by LiOH monohydrate in MeCN/H2O resulted in the corresponding fluorinated nucleosides in good yields, whereas the deprotection of N(1)-α-ribofuranosides under the same conditions unexpectedly yielded 6,2′-O-α-D-anhydronucleosides. 6-Substituted (OMe, NH2) thymine β-ribonucleosides were prepared by the treatment of protected N(1)-β-D-ribosides with nucleophilic agents.

Synthesis of 2-(5-azido-5-deoxy-β-D-ribofuranosyl)-4-methyl-5-nitro-1, 2,3-triazole

The synthesis of 2-(5-azido-5-deoxy-β-D-ribofuranosyl)-4-methyl-5- nitro-1,2,3-triazole has been accomplished in 5 steps starting from D-ribose.

Synthesis of Glycosyl Trifluoroacetates and Their Reactions with Carboxylic Acids

2,3,4,6-Tetra-O-acetyl-1-O-trifluoroacetyl-α-D-glucopyranose was prepared in high yield by treating 1,2,3,4,6-penta-O-acetyl-α- or -β-D-glucopyranose with a mixture of trifluoroacetic acid and its anhydride in the presence of trifluoromethanesulfonic acid or antimony (V) fluoridegraphite catalyst.The reaction of the trifluoroacetate with some carboxylic acids afforded the corresponding 1-O-acyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoses.By a similar procedure, anomeric 1-O-trifluoroacetyl-2,3,5-tri-O-benzoyl- and -2,3,5-tri-O-acetyl-D-ribofuranose were obtained from 1-O-acetyl-2,3,5-tri-O-benzoyl- and 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose respectively, and these trifluoroacetates were allowed to react with some carboxylic acids to yield the corresponding 1-O-acyl-β-D-ribofuranose benzoates and acetates.These products were also prepared by direct fusion of 1-O-acetyl-β-D-ribofuranose benzoate and acetate with carboxylic acids.Keywords-glycosyl trifluoroacetate; glycosyl carboxylate; fusion reaction; tetra-O-acetyl-α-D-glucopyranosyl trifluoroacetate; tri-O-benzoyl-α,β-D-ribofuranosyl trifluoroacetate; tri-O-acetyl-α,β-D-ribofuranosyl trifluoroacetate