139418-97-6

Basic information

• Product Name: 1-[(2R,4S,5R)-5-azido-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-chloropyrimidine-2,4(1H,3H)-dione (non-preferred name)
• Synonyms: 4'-Azido-5-chloro-2'-deoxyuridine
• CAS NO: 139418-97-6
• Molecular Formula: C₉H₁₀ClN₅O₅
• Molecular Weight: 303.6592
• Mol File: 139418-97-6.mol

Chemical Properties

• CAS DataBase Reference: 1-[(2R,4S,5R)-5-azido-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-chloropyrimidine-2,4(1H,3H)-dione (non-preferred name)(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(2R,4S,5R)-5-azido-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-chloropyrimidine-2,4(1H,3H)-dione (non-preferred name)(139418-97-6)
• EPA Substance Registry System: 1-[(2R,4S,5R)-5-azido-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-chloropyrimidine-2,4(1H,3H)-dione (non-preferred name)(139418-97-6)

Safety Data

• Hazardous Substances Data: 139418-97-6(Hazardous Substances Data)

Usage

Type of compound

Heterocyclic compound

Rings present

Pyrimidine-2,4-dione ring and a tetrahydrofuran ring

Functional groups

Azido group and hydroxymethyl group

Azido group

Reactive functional group used in various chemical reactions

Hydroxymethyl group

Provides additional reactivity

Potential applications

Pharmaceuticals, materials science, and organic synthesis

Safety precautions

Should be handled carefully and studied further to understand its properties and potential uses

Stereochemistry

(2R,4S,5R) configuration

Upstream product

• 50-90-8 5-chloro-2'-deoxyuridine 
• 139419-03-7 1-(4-azido-2,5-dideoxy-5-iodo-β-D-erythro-pentofuranosyl)5-chloro-2,4-dioxopyrimidine 
• 111476-39-2 5-chloro-2',5'-dideoxy-5'-iodouridine 
• 139426-40-7 5-chloro-1-(2,5-dideoxy-β-D-glycero-pent-4-enofuranosyl)uracil 
• 140226-27-3 4'-azido-5-chloro-2',5'-dideoxy-5'-iodo-3'-O-(4-methoxybenzoyl)uridine 

Relevant articles and documents

Antiviral agents

Nucleoside compounds of the formula STR1 wherein: B is a purine or a pyrimidine; X and X' are H, OH or F, provided that at least one is H; Y and Y' are H, OH, OCH3 or F, provided that at least one is H; Y' and Z together form a cyclic phosphate ester, provided that Y is H; or Z is STR2 where n is zero, one, two or three; and Z' is N3 or OCH3 ; provided that when X' and Y' are OH and Z' is N3, B is not cytosine, and when X' and Y' are OH and Z' is OCH3, B is not uracil, adenine or cytosine; and the pharmaceutically acceptable esters, ethers and salts thereof, have been found to have potent antiviral activity with a high therapeutic ratio.

Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides

A series of nucleosides were synthesized in which the 4'-hydrogen was substituted with either an azido or a methoxy group. The key steps in the syntheses of the 4'-azido analogues were the stereo- and regioselective addition of iodine azide to a 4'-unsatu