35095-93-3

Basic information

• Product Name: 2-AMINO-6-CHLORO-9-(3,5-DI-O-(P-TOLUOYL)-BETA-D-2-DEOXYRIBOFURNANOSYL)PURINE
• Synonyms: 2-AMINO-6-CHLORO-9-(3,5-DI-O-(P-TOLUOYL)-BETA-D-2-DEOXYRIBOFURNANOSYL)PURINE;2-Amino-6-chloro-9-(2'-deoxy-3',5'-di-O-toluoyl-b-D-ribofuranosyl)purine;2-AMino-6-chloropurine-9-beta-D-(2'-deoxy-3',5'-di-(O-p-toluoyl))riboside;2-AMino-6-chloro-9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-ribofuranosyl)purine;6-Chloro-9-[2-deoxy-3,5-bis-O-(4-methylbenzoyl)-beta-D-erythro-pentofuranosyl]-9H-purin-2-amine;2-Amino-6-chloro-9-(3,5-di-(p-toluoyl)-β-D-2-deoxyribofuranosyl)purine
• CAS NO: 35095-93-3
• Molecular Formula: C₂₆H₂₄ClN₅O₅
• Molecular Weight: 521.95
• Mol File: 35095-93-3.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-AMINO-6-CHLORO-9-(3,5-DI-O-(P-TOLUOYL)-BETA-D-2-DEOXYRIBOFURNANOSYL)PURINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-6-CHLORO-9-(3,5-DI-O-(P-TOLUOYL)-BETA-D-2-DEOXYRIBOFURNANOSYL)PURINE(35095-93-3)
• EPA Substance Registry System: 2-AMINO-6-CHLORO-9-(3,5-DI-O-(P-TOLUOYL)-BETA-D-2-DEOXYRIBOFURNANOSYL)PURINE(35095-93-3)

Safety Data

• Hazardous Substances Data: 35095-93-3(Hazardous Substances Data)

Usage

Chemical Class

Purine nucleoside

Structural Modifications

Position: Chlorine atom at the 6th position
Ribose Sugar Modification: Toluoyl groups at the 3rd and 5th positions

Potential Biological Activities

Antiviral: Possible application in inhibiting viral replication.
Anticancer: Potential for targeting cancer cells or inhibiting tumor growth.
Antiparasitic: Potential activity against parasitic infections.

Potential Pharmaceutical Uses

Drug Development: Useful in creating new pharmaceutical agents.
Diagnostic Agents: Potential in developing diagnostic tools for various diseases.
Therapeutic Agents: Potential for therapeutic interventions in diseases.

Need for Further Research

Requires additional investigation to determine specific properties, mechanisms of action, and potential applications in medicine.

Upstream product

• 7732-18-5 water 
• 10310-21-1 2-Amino-6-chloropurin 
• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 

Downstream Products

• 136986-33-9 6-chloro-9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-ribofuranosyl)-2-p-toluamidopurine 
• 120595-72-4 2-Amino-6-chloro-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine 
• 136986-37-3 9-<2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl>-2-dimethyleneamino-6-methoxyaminopurine 3'-(2-cyanoethyl N,N-di-isopropylphosphoramidite) 
• 136986-36-2 N'-{9-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-6-[(Z)-methoxyimino]-6,9-dihydro-1H-purin-2-yl}-N,N-dimethyl-formamidine 
• 869354-99-4 N'-{9-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-[(Z)-methoxyimino]-6,9-dihydro-1H-purin-2-yl}-N,N-dimethyl-formamidine 
• 68045-42-1 2-Amino-9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1,9-dihydro-purin-6-one O-methyl-oxime 
• 789-61-7 2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine 
• 136986-34-0 2-amino-9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-ribofuranosyl)-6-methoxyaminopurine 

Relevant articles and documents

Substituted purines and oligonucleotide cross-linking

This invention is directed to novel purine-based compounds for inclusion into oligonucleotides. The compounds of the invention, when incorporated into oligonucleotides are especially useful as "antisense" agents--agents that are capable of specific hybrid

A convenient synthesis of 2'-deoxy-6-thioguanosine, ara-guanine, ara-6-thioguanine and certain related purine nucleosides by the stereospecific sodium salt glycosylation procedure [1]

A simple and high-yield synthesis of biologically significant 2'-deoxy-6-thioguanosine, ara-6-thioguanine and araG has been accomplished employing the stereospecific sodium salt glycosylation method. Glycosylation of the sodium salt of 6-chloro- and 2-amino-6-chloropurine (1 and 2, respectively) with 1-chloro-2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranose gave the corresponding N-9 substituted nucleosides as major products with the β-anomeric configuration (4 and 5, respectively) along with a minor amount of the N-7 positional isomers (6 and 7). Treatment of 4 with hydrogen sulfide in methanol containing sodium methoxide gave 2'-deoxy-6-thioinosine in 93% yield. Similarly, 5 was transformed into 2'-deoxy-6-thioguanosine (β-TGdR, 11) in 71% yield. Reaction of the sodium salt of 2 with 1-chloro-2,3,5-tri-O-benzyl-α-D-arabinofuranose gave N-7 and N-9 glycosylated products 13 and 9, respectively. Debenzylation of 9 with boron trichloride at -78° gave the versatile intermediate 2-amino-6-chloro-9-β-D-arabinofuranosylpurine 62% yield. Direct treatment of 14 with sodium hydrosulfide furnished ara-6-thioguanine. Alkaline hydrolysis of 14 readily gave 9-β-D-arabinofuranosylguanine (araG, 17), which on subsequent phosphorylation with phosphorus oxychloride in trimethyl phosphate afforded araG 5'-monophosphate.