23316-67-8

Basic information

• Product Name: 2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl cyanide
• Synonyms: 2,5-Anhydro-D-allononitrile 3,4,6-Tribenzoate;2,3,5-TRI-O-BENZOYL-BETA-D-RIBOFURANOSYL CYANIDE;2,5-ANHYDRO-3,4,6-TRI-O-BENZOYL-D-ALLONONITRILE;2,3,5-Tri-O-benzoyl-β-D-ribofuranosylcyanide;2,3,5-Tri-O-benzoyl-b-D-ribofuranosylcyanide;(2R,3R,4S,5S)-2-(benzoyloxymethyl)-5-cyanotetrahydrofuran-3,4-diyl dibenzoate
• CAS NO: 23316-67-8
• Molecular Formula: C₂₇H₂₁NO₇
• Molecular Weight: 471.46
• Mol File: 23316-67-8.mol
• Article Data: 31

Chemical Properties

• Boiling Point: 643.1 °C at 760 mmHg
• Flash Point: 272.4 °C
• Appearance: /
• Density: 1.35 g/cm³
• Vapor Pressure: 1.96E-16mmHg at 25°C
• Refractive Index: 1.624
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• BRN: 1443499
• CAS DataBase Reference: 2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl cyanide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl cyanide(23316-67-8)
• EPA Substance Registry System: 2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl cyanide(23316-67-8)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 23316-67-8(Hazardous Substances Data)

Usage

Uses

2,5-Anhydro-D-allononitrile 3,4,6-Tribenzoate is an intermediate in the synthesis of Tiazofurin (T437200), which is a potential therapeutic agent in the treatment of cancer.

InChI:InChI=1/C27H21NO7/c28-16-21-23(34-26(30)19-12-6-2-7-13-19)24(35-27(31)20-14-8-3-9-15-20)22(33-21)17-32-25(29)18-10-4-1-5-11-18/h1-15,21-24H,17H2/t21-,22+,23-,24+/m0/s1

Upstream product

• 82225-18-1 3,5-di-O-benzoyl-1,2-O-(1-cyanobenzylidene)-β-ribofuranose 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 7677-24-9 trimethylsilyl cyanide 
• 107-06-2 1,2-dichloro-ethane 
• 14215-97-5 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose 
• 58-63-9 Inosine 
• 98-88-4 benzoyl chloride 
• 22860-91-9 2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide 
• 4099-85-8 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 5517-60-2 methyl 3'-O-benzoyl-2,3-O-isopropylidene-β-D-apiofuranoside 
• 5517-61-3 methyl 3'-O-benzoyl-β-D-apiofuranoside 
• 52783-53-6 methyl 2,3,3'-tri-O-benzoyl-β-D-apiofuranoside 
• 50720-88-2 2,5-anhydro-3,4,6-tri-O-benzoyl-β-D-allose oxime 
• 29706-90-9 β-D-2,3,5-tri-O-benzoylribofuranosyl chloride 

Downstream Products

• 63128-94-9 (1S)-tri-O-benzoyl-1-(1⁽²⁾H-tetrazol-5-yl)-D-1,4-anhydro-ribitol 
• 38642-52-3 benzyl 2,3,5-tri-O-benzoyl-D-ribofuranosylthioformimidate hydrochloride 
• 38716-29-9 benzyl 2,5-anhydro-3,4,6-tri-O-benzoyl-D-allonothioimidate hydrochloride 
• 57944-10-2 2,5-anhydro-3,4,6-tri-O-benzoyl-D-allonthioamide 
• 477881-06-4 methyl 1'-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)thiazoline-4'-carboxylate 

Relevant articles and documents

A modified synthesis of tiazofurin

An improved synthesis of tiazofurin is described from 1-O-acetyl-2,3,5- tri-O-benzoyl-β-D-ribofuranose.

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A series of novel aminoacyl adenylate mimics has been prepared and evaluated for their inhibitory activity against aminoacyl-tRNA synthetases. Several of these thiazole derivatives displayed potent and selective enzyme activity against both Gram-positive and Gram-negative bacteria.

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