3510-73-4

Basic information

• Product Name: 6-chloro-9-(2,3,5-tri-O-benzoylpentofuranosyl)-9H-purine
• CAS NO: 3510-73-4
• Molecular Formula: C₃₁H₂₃ClN₄O₇
• Molecular Weight: 598.9899
• Mol File: 3510-73-4.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 760.8°C at 760 mmHg
• Flash Point: 413.9°C
• Density: 1.45g/cm³
• Vapor Pressure: 4.79E-23mmHg at 25°C
• Refractive Index: 1.682
• CAS DataBase Reference: 6-chloro-9-(2,3,5-tri-O-benzoylpentofuranosyl)-9H-purine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-chloro-9-(2,3,5-tri-O-benzoylpentofuranosyl)-9H-purine(3510-73-4)
• EPA Substance Registry System: 6-chloro-9-(2,3,5-tri-O-benzoylpentofuranosyl)-9H-purine(3510-73-4)

Safety Data

• Hazardous Substances Data: 3510-73-4(Hazardous Substances Data)

Usage

Type

Synthetic purine nucleoside analog

Use

Chemotherapeutic agent for certain types of leukemia

Mechanism of action

Interferes with DNA synthesis and repair, leading to inhibition of cell growth and division

Administration

Intravenously

Main indication

Treatment of relapsed or refractory acute lymphoblastic leukemia in pediatric patients

Chemical structure

Purine base with a chloro group at the 6-position and a 2,3,5-tri-O-benzoylpentofuranosyl side chain attached to the 9-position

Importance

Critical drug in the treatment of leukemia, showing promising results in clinical trials.

Upstream product

• 7306-68-5 6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine 
• 99395-04-7 1-O-acetyl-2,3,5-tri-O-benzoyl-D-xylofuranose 
• 87-42-3 6-chloropurine 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 5991-01-5 2,3,5-(tri-O-benzoyl)-D-ribofuranosyl chloride 
• 152279-03-3 Pent-4-enyl β-D-erythro-pentofuranoside 
• 532-20-7 D-Ribose 
• 58-63-9 inosine 
• 98-88-4 benzoyl chloride 
• 14215-97-5 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose 
• 2004-06-0 6-Chloropurine riboside 
• 152279-04-4 Pent-4-enyl 2',3',5'-tri-O-benzoyl-β-D-erythro-pentofuranoside 
• 6741-88-4 2',3',5'-tri-O-benzoylinosine 

Downstream Products

• 79366-24-8 9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-9H-purine 
• 1526929-34-9 C₃₁H₂₆N₆O₇ 
• 66048-54-2 3',5'-di-O-benzoyl-N⁶-benzyladenosine 
• 74829-54-2 3',5'-di-O-benzoyl-N⁶-benzyl-2'-O-m-toluoyladenosine 
• 74829-55-3 2',5'-di-O-benzoyl-N⁶-benzyl-3'-O-m-toluoyladenosine 
• 69471-67-6 2',5'-di-O-benzoyl-N⁶-benzyladenosine 
• 6741-88-4 2',3',5'-tri-O-benzoylinosine 
• 71118-18-8 C₃₃H₂₇N₅O₈ 
• 73619-40-6 C₃₄H₂₆N₆O₇ 
• 161084-90-8 9-(2,5-di-O-trityl-β-D-xylofuranosyl)-N⁶-cyclopentyladenine 
• 161084-91-9 2',5'-di-O-trityl-3'-fluoro-3'-deoxy-N⁶-cyclopentyladenosine 
• 51375-21-4 (2R,3R,4S,5R)-2-[6-(4-Chloro-benzylsulfanyl)-purin-9-yl]-5-hydroxymethyl-tetrahydro-furan-3,4-diol 

Relevant articles and documents

METHOD FOR SYNTHESIZING DIVERSELY SUBSTITUTED PURINES

The present invention relates to a method for synthesizing diversely substituted purines starting from a pyrimidine. Formula (I). The method comprises the formation of an amidine group on the pyrimidine by implementing a Vilsmeier type reagent, the functi

High-throughput five minute microwave accelerated glycosylation approach to the synthesis of nucleoside libraries

The Vorbrueggen glycosylation reaction was adapted into a one-step 5 min/130 °C microwave assisted reaction. Triethanolamine in acetontrile containing 2% water was determined to be optimal for the neutralization of trimethylsilyl inflate allowing for direct MPLC purification of the reaction mixture. When coupled with a NH3/methanol deprotection reaction, a high-throughput method of nucleoside library synthesis was enabled. The method was demonstrated by examining the ribosylation of 48 nitrogen containing heteroaromatic bases that included 25 purines, four pyrazolopyrimidines, two 8-azapurines, one 2-azapurine, two imidazopyridines, two benzimidazoles, three imidazoles, three 1,2,4-triazoles, two pyrimidines, two 3-deazapyrimidines, one quinazolinedione, and one alloxazine. Of these, 32 yielded single regioisomer products, and six resulted in separable mixtures. Seven examples provided inseparable regioisomer mixtures of -two to three compounds (16 nucleosides), and three examples failed to yield isolable products. For the 45 single isomers isolated, the average two-step overall yield ± SD was 26 ± 16%, and the average purity ± SD was 95 ± 6%. A total of 58 different nucleosides were prepared of which 15 had not previously been accessed directly from glycosylation/deprotection of a readily available base.

Introduction of a benzoyl group onto riboside in aqueous solution: One- step synthesis of 6-chloropurine 2',3'-di-O-benzoylriboside

A benzoyl group was introduced onto the 3'-hydroxyl group of 6- chloropurine riboside by treatment with benzoylating agents in the presence of an organic or inorganic base in aqueous solution, in which further reaction gave 6-chloropurine 2',3'-di-O-benzo