124939-87-3

Basic information

• Product Name: methyl 5-O-benzyl-2-O-benzoyl-3-fluoro-3-deoxy-α-D-ribofuranoside
• Synonyms: methyl 5-O-benzyl-2-O-benzoyl-3-fluoro-3-deoxy-α-D-ribofuranoside
• CAS NO: 124939-87-3
• Molecular Weight: 360.382
• Mol File: 124939-87-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: methyl 5-O-benzyl-2-O-benzoyl-3-fluoro-3-deoxy-α-D-ribofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 5-O-benzyl-2-O-benzoyl-3-fluoro-3-deoxy-α-D-ribofuranoside(124939-87-3)
• EPA Substance Registry System: methyl 5-O-benzyl-2-O-benzoyl-3-fluoro-3-deoxy-α-D-ribofuranoside(124939-87-3)

Safety Data

• Hazardous Substances Data: 124939-87-3(Hazardous Substances Data)

Upstream product

• 7045-40-1 Methyl 3,5-O-Isopropylidene-α-D-xylofuranoside 
• 26532-10-5 methyl 2,3-anhydro-α-D-lyxofuranoside 
• 14980-09-7 methyl 5-O-benzyl-3-fluoro-3-deoxy-α-D-arabino-furanoside 
• 98-88-4 benzoyl chloride 
• 582-25-2 Potassium benzoate 
• 126716-23-2 methyl 5-O-benzyl-2-O-tosyl-3-fluoro-3-deoxy-α-D-arabino-furanoside 

Downstream Products

• 123484-12-8 ((2R,3R,4S)-5-acetoxy-4-(benzoyloxy)-3-fluorotetrahydrofuran-2-yl)methyl benzoate 
• 126716-27-6 methyl 2,5-di-O-benzoyl-3-fluoro-3-deoxy-α-D-ribofuranoside 
• 133776-16-6 C₃₆H₄₂FN₅O₇ 
• 133776-15-5 C₃₆H₄₂FN₅O₇ 
• 112668-60-7 N6-benzoyl-9-(2'-O-benzoyl-3'-deoxy-3'-fluoro-β-D-ribofuranosyl)adenine 
• 133776-14-4 C₂₆H₂₂FN₅O₇ 
• 133776-12-2 C₂₃H₁₉FN₂O₇ 
• 112668-58-3 1-(2,5-di-O-benzoyl-3-deoxy-3-fluoro-β-D-ribofuranosyl)uracil 
• 133776-13-3 C₂₃H₂₀FN₃O₆ 
• 123402-21-1 2-amino-9-((2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,9-dihydro-6H-purine-6-one 
• 123402-20-0 3'-deoxy-3'-fluorocytidine 
• 75059-22-2 (2R,3S,4S,5R)-2-(6-amino-9H-purine-9-yl)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-3-ol 
• 126737-61-9 methyl 2-O-benzoyl-3-fluoro-3-deoxy-α-D-ribofuranoside 

Relevant articles and documents

Oxidation-reduction sequence for the synthesis of peracylated fluorodeoxy pentofuranosides

The oxidation of methyl 5-O-benzyl-3(2)-deoxy-3(2)-fluoro-α-D-pentofuranosides with dimethyl sulfoxide-acetic (trifluoroacetic) anhydride was accompanied by epimerization at the carbon atom bearing a fluoro function, resulting in the formation of the corresponding 2- or 3-keto derivatives as mixtures of two epimers in high combined yield.Reduction of a mixture of the erythro/threo epimeric 2-keto sugars (isolated as stable hydrates) with sodium borohydride in benzene-ethanol proceeded stereoselectively leading to the formation of 3-deoxy-3-fluoro ribo- and lyxo-furanosides, respectively.In the case of the ribo and arabino epimers of the 3-keto sugar (isolated as free ketones), reduction stereoselectivity of the former was >95percent for the 2-deoxy-2-fluoro ribo sugar, whereas a ca. 3:1 lyxo/arabino ratio of products was obtained for the latter.Treatment of a mixture of the 2-epimeric 3-keto sugars with triethylamine in carbon tetrachloride at room temperature for 3-5 h afforded the 2-deoxy-2-fluoro ribo ketone (ca. 90percent).The synthesis of 1-O-acetyl-2,5-di-O-benzoyl-3-deoxy-3-fluoro-α,β-D-lyxofuranose (8) and 1-O-acetyl-3,5-di-O-benzoyl-2-deoxy-2-fluoeo-β-D-ribofuranose (16) and their use as glycosylating agents for bis-trimethylsilylated N6-benzoyladenine is described.Keywords: Fluorodeoxy pentafuranosides; Keto sugars; Epimerization