182825-16-7

Basic information

• Product Name: methyl 2,3,5-tri-O-benzoyl-3-C-ethynyl-α,β-D-ribofuranose
• Synonyms: methyl 2,3,5-tri-O-benzoyl-3-C-ethynyl-α,β-D-ribofuranose
• CAS NO: 182825-16-7
• Molecular Weight: 500.505
• Mol File: 182825-16-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: methyl 2,3,5-tri-O-benzoyl-3-C-ethynyl-α,β-D-ribofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3,5-tri-O-benzoyl-3-C-ethynyl-α,β-D-ribofuranose(182825-16-7)
• EPA Substance Registry System: methyl 2,3,5-tri-O-benzoyl-3-C-ethynyl-α,β-D-ribofuranose(182825-16-7)

Safety Data

• Hazardous Substances Data: 182825-16-7(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 
• 103931-45-9 5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose 
• 98-88-4 benzoyl chloride 

Downstream Products

• 182825-17-8 1-O-acetyl-2,3,5-tri-O-benzoyl-3-C-ethynyl-D-ribofuranose 
• 180300-42-9 1-(2,3,5-tri-O-benzoyl-3-C-ethynyl-β-D-ribofuranosyl)cytosine 
• 180300-43-0 3'-ethynylcytidine 
• 180300-46-3 1-(2,3,5-tri-O-benzoyl-3-C-ethynyl-β-D-ribofuranosyl)uracil 

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.

Nucleosides and nucleotides. 152. 1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)uracil as a broad spectrum antitumor nucleoside

1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)uracil (EUrd) has been designed as a potential multifunctional antitumor nucleoside antimetabolite. EUrd was synthesized by condensation of 1-O-acetyl-2,3,5-tri-O-benzoyl-3-C-ethynyl-α,β-D-ribo-pentofuranose (6) and bis(trimethylsilyl)uracil in the presence of trimethylsilyl triflate in CH3CN in good yield, followed by debenzoylation with NH3/MeOH. In vitro tumor cell growth inhibitory activity of EUrd against 14 human solid tumor cell lines was compared with 5-fluorouridine (FUrd), 2'-deoxy-5-fluorouridine (FdUrd), and 5-fluorouracil (5-FU) as positive controls. EUrd was a quite potent tumor cell growth inhibitor against almost all the tumor cell lines examined in this study except for human pancreas PANC-1 cells, and the potency of EUrd is about 6 to 650 times stronger than that of 5-FU and comparable to that of FUrd and FdUrd. EUrd showed also potent antitumor activity against human tumors as xenografts in nude mice when given in a daily intravenous dose of 2 mg/kg on consecutive days.