69339-86-2

Basic information

• Product Name: 1,2,3,5-tetra-O-benzoyl-α-D-ribofuranoside
• Synonyms: 1,2,3,5-tetra-O-benzoyl-α-D-ribofuranoside
• CAS NO: 69339-86-2
• Molecular Weight: 566.564
• Mol File: 69339-86-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1,2,3,5-tetra-O-benzoyl-α-D-ribofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,5-tetra-O-benzoyl-α-D-ribofuranoside(69339-86-2)
• EPA Substance Registry System: 1,2,3,5-tetra-O-benzoyl-α-D-ribofuranoside(69339-86-2)

Safety Data

• Hazardous Substances Data: 69339-86-2(Hazardous Substances Data)

Upstream product

• 32445-75-3 D-Ribose 
• 98-88-4 benzoyl chloride 
• 5991-01-5 2,3,5-(tri-O-benzoyl)-D-ribofuranosyl chloride 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 22224-41-5 1,3,5-tri-O-benzoyl-α-D-ribofuranoside 

Downstream Products

• 22860-91-9 2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide 
• 23643-36-9 2′,3′,5′-tri-O-benzoyl-2′-C-methyluridine 
• 1443997-55-4 (2R,3R,4R,5R)-5-((benzoyloxy)methyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-ethynyltetrahydrofuran-3,4-diyldibenzoate 
• 1044589-96-9 (2R,3R,4R,5R)-5-((benzoyloxy)methyl)-3-ethynyl-3-hydroxytetrahydrofuran-2,4-diyl dibenzoate 
• 1443997-56-5 C₂₃H₂₈N₃O₉PS 
• 1443997-57-6 C₂₃H₂₈N₃O₉PS 
• 1443998-10-4 C₅₃H₄₀ClN₅O₈ 
• 1443998-09-1 C₃₃H₂₄ClN₅O₇ 

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.

Radical Rearrangement of 2-O-(Diphenylphosphoryl)glycosyl Bromides. A New Synthesis for 2-Deoxy Disaccharides and 2-Deoxy Ribonucleosides

2-Deoxy-1-O-diphenylphosphoryl glycosides react with nucleophiles under mild conditions giving access to 2-deoxy disaccharides and nucleosides.The intermediate 2-deoxy-1-O-diphenylphosphoryl compounds were generated in situ by a radical 2 -> 1 migration of the phosphate ester group.This is the first observation of a rearrangement of a phosphate ester in radicals.ESR experiments and quenching of the radical at C2 by tin hydride or tin deuteride were used to detect the intermediates and to prove their structure.