91713-46-1

Basic information

• Product Name: 6-CHLORO-9-(3,5-O-DI(P-TOLUOYL)-BETA-D-2-DEOXYRIBOFURANOSYL) PURINE
• Synonyms: 6-CHLORO-9-(3,5-O-DI(P-TOLUOYL)-BETA-D-2-DEOXYRIBOFURANOSYL) PURINE;6-Chloro-9-(2'-deoxy-3',5'-di-O-toluoyl-b-ribofuranosyl)purine;3,5-O-Ditoluoyl 6-Chloropurine-9-β-D-deoxyriboside;6-Chloro-9-(2'-deoxy-3',5'-di-O-toluoyl-β-ribofuranosyl)purine;6-Chloro-9-[2-deoxy-3,5-bis-O-(4-Methylbenzoyl)-β-D-erythro-pentofuranosyl]purine
• CAS NO: 91713-46-1
• Molecular Formula: C₂₆H₂₃ClN₄O₅
• Molecular Weight: 506.94
• Product Categories: Bases & Related Reagents;Intermediates;Nucleotides
• Mol File: 91713-46-1.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: 6-CHLORO-9-(3,5-O-DI(P-TOLUOYL)-BETA-D-2-DEOXYRIBOFURANOSYL) PURINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLORO-9-(3,5-O-DI(P-TOLUOYL)-BETA-D-2-DEOXYRIBOFURANOSYL) PURINE(91713-46-1)
• EPA Substance Registry System: 6-CHLORO-9-(3,5-O-DI(P-TOLUOYL)-BETA-D-2-DEOXYRIBOFURANOSYL) PURINE(91713-46-1)

Safety Data

• Hazardous Substances Data: 91713-46-1(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Foam

Uses

A protected purine deoxynucleoside DNA adduct.

Upstream product

• 73349-28-7 sodium salt of 6-chloropurine 
• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 87-42-3 6-chloropurine 
• 3601-89-6 Hoffer's chlorosugar 
• 756494-13-0 2'-deoxy-3',5'-di-O-(4-methylbenzoyl)inosine 
• 874-60-2 4-methyl-benzoyl chloride 
• 452-51-7 D-2-deoxyribose 
• 87-42-3 6-chloro-7H-purine 
• 890-38-0 2-deoxyinosine 

Downstream Products

• 136986-35-1 2'-deoxy-N⁶-methoxy-3',5'-di-O-p-toluoyladenosine 
• 132183-37-0 2'-Deoxy-N⁶-(1-pyrenylmethyl)-3',5'-di-O-p-toluoyladenosine 
• 4594-45-0 6-chloropurine-2'-deoxyriboside 
• 2239-64-7 6-mercaptopurine-2’-deoxyribose 
• 958-09-8 2'-deoxy-D-adenosine 
• 35665-58-8 N⁶,N⁶-dimethyl-2'-deoxyadenosine 
• 328378-38-7 9-[2-deoxy-3,5-di-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-6-(4-fluorophenyl)purine 
• 328378-39-8 9-[2-deoxy-3,5-di-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-6-(4-methoxyphenyl)purine 
• 181475-59-2 9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-6-methylpurine 
• 328378-37-6 9-[2-deoxy-3,5-di-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-6-phenylpurine 
• 756494-16-3 9-[2-deoxy-3,5-di-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-6-iodopurine 
• 852677-21-5 9-[2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-6-[(trimethylsilyl)ethynyl]purine 
• 773133-86-1 6-(acetyloxymethyl)-9-(2-deoxy-3,5-di-O-(p-toluolyl)-β-D-erythro-pentofuranosyl)purine 
• 863887-14-3 C₃₁H₂₇N₅O₅ 

Relevant articles and documents

Method for synthesizing cladribine through nitration-chlorination method

The invention discloses a novel method for synthesizing cladribine through a nitration-chlorination method. According to the method, cheap 6-chloropurine and 1-chloro-2,3,5-tris-O-p-chlorobenzoyl-D-ribose are taken as raw materials, sodium hydride is taken as alkali, acetonitrile is taken as reaction solvent, and a beta isomer is obtained through a high-selectivity reaction; the obtained beta isomer does not need to remove protecting groups, the beta isomer reacts with trifluoromethanesulfonic anhydride after being separated, and nitryl is introduced at the second position; the nitryl is transformed into chlorine atoms in an ethanol solution of NH4Cl; two steps of reactions of protecting group removal and chlorine atom ammonolysis are completed in a methanol solution saturated by ammonia gas, and then the cladribine is obtained through four steps at the total yield of 78%. The method has the advantages that the raw materials are low in cost and easy to obtain, the technology is simple and convenient, the total yield is higher, the cost is low, amplification is easy, expensive reagents and poisonous and harmful heavy metal catalysts are prevented from being used, and when the reaction scale is expanded to the 100-g scale, the yield is not decreased obviously. A novel synthesizing path is supplied to synthesizing of the cladribine, and the potential application prospect is achieved.

Synthesis of 6-substituted purine N7-(2-deoxy-β-D-ribonucleosides) via anion glycosylation and anomerization during the N7/N9-glycosyl transfer

The synthesis of the 7-(2-deoxy-β-D-erythro-pentofuranosyl)adenine (1b) as well as the corresponding hypoxanthine- and purine nucleosides 3 and 4 is described employing the stereoselective nucleobase anion glycosylation. The N7/N9-is

FACILE STEREOSPECIFIC SYNTHESIS OF α-ANOMERIC 2'-DEOXYNUCLEOSIDES

The coupling reaction of activated nucleobases, such as the sodium salts of N-benzoyladenine and 6-chloropurine and 2,4-bis-O-trimethylsilylthymine, with 1-α-chloro-2-deoxy-3,5-di-O-p-toluoylribofuranose (1) in a mixture of acetonitrile and tetrahydrofuran leads to the stereospecific formation of α-anomeric 2'-deoxynucleosides with satisfactory yields.The ratio of the distribution between the resulted α- and β-stereoisomers was about 3:1 in each case.The method is simple and applicable to the preparation of both purine and pyrimidine α-2'-deoxynucleosides.