70042-26-1

Basic information

• Product Name: 1-(2,3,4-tri-O-acetylpentopyranosyl)-1H-imidazole-4,5-dicarbonitrile
• CAS NO: 70042-26-1
• Molecular Formula: C₁₆H₁₆N₄O₇
• Molecular Weight: 376.3208
• Mol File: 70042-26-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 593°C at 760 mmHg
• Flash Point: 312.4°C
• Density: 1.46g/cm³
• Vapor Pressure: 4.95E-14mmHg at 25°C
• Refractive Index: 1.613
• CAS DataBase Reference: 1-(2,3,4-tri-O-acetylpentopyranosyl)-1H-imidazole-4,5-dicarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,3,4-tri-O-acetylpentopyranosyl)-1H-imidazole-4,5-dicarbonitrile(70042-26-1)
• EPA Substance Registry System: 1-(2,3,4-tri-O-acetylpentopyranosyl)-1H-imidazole-4,5-dicarbonitrile(70042-26-1)

Safety Data

• Hazardous Substances Data: 70042-26-1(Hazardous Substances Data)

Usage

Description

1-(2,3,4-tri-O-acetylpentopyranosyl)-1H-imidazole-4,5-dicarbonitrile is a complex chemical compound featuring a pentopyranosyl group linked to an imidazole ring, which is further attached to two carbonitrile groups. The pentopyranosyl group is acetylated at three hydroxyl positions, resulting in a highly functionalized molecule with potential applications in the pharmaceutical industry and biochemical research.

Uses

Used in Pharmaceutical Industry:
1-(2,3,4-tri-O-acetylpentopyranosyl)-1H-imidazole-4,5-dicarbonitrile is used as a key intermediate for the development of new drugs due to its unique structure and functional groups, which may offer interesting properties for further investigation and potential use in various fields of scientific research and industry.
Used in Biochemical Research:
In the field of biochemical research, 1-(2,3,4-tri-O-acetylpentopyranosyl)-1H-imidazole-4,5-dicarbonitrile serves as a valuable compound for studying its interactions with biopolymers and macromolecules, potentially leading to advancements in understanding complex biological processes and the development of novel therapeutic strategies.

Upstream product

• 1122-28-7 4,5-dicyano-1H-imidazole 
• 4627-30-9 (3R,4R,5R)-tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate 
• 71772-49-1 D-ribopyranosyldiaminomaleonitrile 
• 10257-32-6 D-ribose 
• 70042-24-9 N-(2',3',4'-tri-O-acetyl-D-ribopyranosyl)diaminomaleonitrile 
• 122-51-0 orthoformic acid triethyl ester 

Relevant articles and documents

Nucleosides from Carbohydrate Adducts of Diaminomaleonitrile. A Novel Synthesis of 5-Amino-1-(β-D-ribofuranosyl)imidazole-4-carboxamide and 5-Amino-1-(β-D-ribopyranosyl)imidazole-4-carboxamide

The stereospecific and regiospecific synthesis of 5-amino-1-(β-D-ribofuranosyl)imidazole-4-carboxamide (16) was achieved in six steps.A key intermediate in the synthesis, N-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)diaminomaleonitrile (3), was prepared by two routes: the reaction of diaminomaleonitrile (1) with 1-bromo-2,3,5-tri-O-benzoyl-β-D-ribofuranose (2) and the reaction of the bis(trimethylsilyl) derivative of diaminomaleonitrile (4) with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (5).Reaction of 3 triethyl orthoformate yielded 4,5-dicyano-1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)imidazole (10).Alternatively 10 was synthesized by the acid-catalyzed cyclization of the N-formyl derivative 12 which was prepared by the reaction of the trimethylsilyl derivative of N-formyldiaminomaleonitrile 11 with 5.Deblocking 10 with 1 equiv of sodium methoxide at room temperature resulted in the regiospecific formation of the 5-imidate 14.Reaction of 14 with alkaline hypochlorite yielded 5-amino-1-(β-D-ribofuranosyl)imidazole-4-carbonitrile (15) by a Hofmann rearrangement.Alkaline hydrolysis of the nitrile function yielded the corresponding amide 16. 5-Amino-1-(β-D-ribopyranosyl)imidazole-4-carboxamide (28) was prepared by a similar synthetic sequence.Reaction of diaminomaleonitrile (1) with ribose gave a mixture of the α- and β-anomers of D-ribopyranosyldiaminomaleonitrile (17).Compound 17 was converted to a mixture of the anomeric tri-O-acetates which on heating with triethyl orthoformate gave a separable mixture of the α- and β-anomers of 4,5-dicyano-1-(2',3',4'-tri-O-acetyl-D-ribopyranosyl)imidazole (19 and 20, respectively).Reaction of 19 with NH3/CH3OH at room temperature cleaved the three acetyl groups and regiospecifically converted the 5-cyano to the 5-imidate (26).The regiospecificity is due to the attack of the 2'-oxy anion on the 5-cyano group as shown by the isolation of the cyclic imidate 25 when the reaction is carried out at 0 deg C.The Hofmann rearrangement of imidate 26 followed by alkaline hydrolysis gave 5-amino-1-(β-D-ribopyranosyl)imidazole-4-carbonitrile 27 and 28, respectively.The 1H and 13C NMR spectra of imidates 14 and 26 have multiple peaks for the protons and carbons, respectively.Restricted rotation of the 5-imidate (energy of activation 18 kcal) results in isomers of 14 and 26 with different NMR spectra.The C-2, H-1' coupling constants of 2.5-3.1 Hz of the isomeric species comprising imidates 14 and 26 are consistent with a H-2, H-1' dihedral angle of 135 deg and an anti orientation of the imidazole with respect to the ribose ring; a conclusion confirmed by NOE measurements.