182825-17-8

Basic information

• Product Name: 1-O-acetyl-2,3,5-tri-O-benzoyl-3-C-ethynyl-D-ribofuranose
• Synonyms: 1-O-acetyl-2,3,5-tri-O-benzoyl-3-C-ethynyl-D-ribofuranose
• CAS NO: 182825-17-8
• Molecular Weight: 528.515
• Mol File: 182825-17-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1-O-acetyl-2,3,5-tri-O-benzoyl-3-C-ethynyl-D-ribofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O-acetyl-2,3,5-tri-O-benzoyl-3-C-ethynyl-D-ribofuranose(182825-17-8)
• EPA Substance Registry System: 1-O-acetyl-2,3,5-tri-O-benzoyl-3-C-ethynyl-D-ribofuranose(182825-17-8)

Safety Data

• Hazardous Substances Data: 182825-17-8(Hazardous Substances Data)

Upstream product

• 155470-62-5 5-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-3-C-(2-trimethylsilylethynyl)-α-D-ribofuranose 
• 180300-78-1 ((3aR,5R,6R,6aR)-6-ethynyl-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate 
• 182825-15-6 methyl 5-O-benzoyl-3-C-ethynyl-α,β-D-ribofuranose 
• 155470-63-6 3-C-ethynyl-1,2-O-isopropylidene-α-D-ribo-pentofuranose 
• 103931-45-9 5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose 
• 98-88-4 benzoyl chloride 
• 108-24-7 acetic anhydride 
• 182825-16-7 methyl 2,3,5-tri-O-benzoyl-3-C-ethynyl-α,β-D-ribofuranose 

Downstream Products

• 180300-46-3 1-(2,3,5-tri-O-benzoyl-3-C-ethynyl-β-D-ribofuranosyl)uracil 
• 180300-47-4 1-(2,3,5-tri-O-benzoyl-3-C-ethynyl-β-D-ribofuranosyl)-5-fluorouracil 
• 180300-42-9 1-(2,3,5-tri-O-benzoyl-3-C-ethynyl-β-D-ribofuranosyl)cytosine 
• 180300-51-0 1-(2,3,5-tri-O-benzoyl-3-C-ethynyl-β-D-ribofuranosyl)thymine 
• 1053698-55-7 C₃₅H₂₆N₄O₈ 
• 180300-43-0 3'-ethynylcytidine 

Relevant articles and documents

Nucleosides and nucleotides. Part 212: Practical large-scale synthesis of 1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)cytosine (ECyd), a potent antitumor nucleoside. Isobutyryloxy group as an efficient anomeric leaving group in the Vorbrüggen glycosylation reaction

A practical synthetic route to the antitumor nucleoside, 1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)cytosine (ECyd, 1) from 1,2-O-isopropylidene-D-xylofuranose (3) has been developed. Since most of the compounds were obtained as crystals, the target ECyd was prepared without any chromatographic purification in 31% overall yield from compound 3. The isobutyryloxy group was found to be an effective leaving group at the anomeric position of the 3-β-C-ethynyl glycosyl donors in the key Vorbru?ggen glycosylation reaction. Using a similar procedure without chromatographic purification, the uracil congener EUrd [1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)uracil (2), which also has a potent antitumor effect, was synthesized from 3 in 39% overall yield.