1294481-82-5

Basic information

• Product Name: 9-[(2R)-3,5-bis-O-(4-Chlorobenzoyl)-2-deoxy-2-fluoro-2-Methyl-b-D-erythro-pentofuranosyl]-6-chloro-9H-purin-2-aMine
• Synonyms: 9-[(2R)-3,5-bis-O-(4-Chlorobenzoyl)-2-deoxy-2-fluoro-2-Methyl-b-D-erythro-pentofuranosyl]-6-chloro-9H-purin-2-aMine;9-[(2R)-3,5-Bis-O-(4-chlorobenzoyl)-2-deoxy-2-fluoro-2-methyl-beta-D-erythro-pentofuranosyl]-6-chloro-9H-purin-2-amine;(2R,3R,4R,5R)-5-(2-Amino-6-chloro-9H-purin-9-yl)-2-[(4-chlorobenzoyloxy)methyl]-4-fluoro-4-methyloxolan-3-yl 4-chlorobenzoate;(2R,3R,4R,5R)-5-(2-Amino-6-chloro-9H-purin-9-yl)-2-(((4-chlorobenzoyl)oxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl 4-chlorobenzoate
• CAS NO: 1294481-82-5
• Molecular Formula: C₂₅H₁₉Cl₃FN₅O₅
• Molecular Weight: 594.8062632
• Mol File: 1294481-82-5.mol

Chemical Properties

• Melting Point: 171-176℃
• Boiling Point: 759.4±70.0 °C(Predicted)
• Appearance: /
• Density: 1.63
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 1.69±0.10(Predicted)
• CAS DataBase Reference: 9-[(2R)-3,5-bis-O-(4-Chlorobenzoyl)-2-deoxy-2-fluoro-2-Methyl-b-D-erythro-pentofuranosyl]-6-chloro-9H-purin-2-aMine(CAS DataBase Reference)
• NIST Chemistry Reference: 9-[(2R)-3,5-bis-O-(4-Chlorobenzoyl)-2-deoxy-2-fluoro-2-Methyl-b-D-erythro-pentofuranosyl]-6-chloro-9H-purin-2-aMine(1294481-82-5)
• EPA Substance Registry System: 9-[(2R)-3,5-bis-O-(4-Chlorobenzoyl)-2-deoxy-2-fluoro-2-Methyl-b-D-erythro-pentofuranosyl]-6-chloro-9H-purin-2-aMine(1294481-82-5)

Safety Data

• Hazardous Substances Data: 1294481-82-5(Hazardous Substances Data)

Usage

Uses

Used in Antiviral Applications:
9-[(2R)-3,5-bis-O-(4-Chlorobenzoyl)-2-deoxy-2-fluoro-2-Methyl-b-D-erythro-pentofuranosyl]-6-chloro-9H-purin-2-aMine is used as an antiviral agent for its ability to interfere with the replication process of various viruses. Its modified structure may contribute to increased resistance to enzymatic degradation, potentially improving its bioavailability and therapeutic effectiveness in combating viral infections.
Used in Antitumor Applications:
In the field of oncology, 9-[(2R)-3,5-bis-O-(4-Chlorobenzoyl)-2-deoxy-2-fluoro-2-Methyl-b-D-erythro-pentofuranosyl]-6-chloro-9H-purin-2-aMine is utilized as an antitumor agent, where it can inhibit the growth of tumor cells. The exact mechanisms of its antitumor activity are under investigation, but its potential to disrupt essential cellular processes in cancer cells makes it a promising candidate for cancer treatment.
Used in Pharmaceutical Industry:
9-[(2R)-3,5-bis-O-(4-Chlorobenzoyl)-2-deoxy-2-fluoro-2-Methyl-b-D-erythro-pentofuranosyl]-6-chloro-9H-purin-2-aMine is used as a pharmaceutical compound for its potential to be developed into drugs targeting viral diseases and cancer. The ongoing research aims to understand its mechanisms of action and optimize its therapeutic potential, with the goal of improving patient outcomes in these critical health areas.
Further research is necessary to fully explore the potential uses and mechanisms of action of this synthetic nucleoside analog, with the aim of advancing its application in medical treatments.

Upstream product

• 1199809-22-7 ((2R,3R,4R,5R)-3-(benzoyloxy)-4-fluoro-5-hydroxy-4-methyltetrahydrofuran-2-yl)methyl benzoate 
• 10310-21-1 2-amino-6-chloropurine 
• 874638-80-9 ((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate 
• 1294481-81-4 (2R,3R,4R,5R)-5-bromo-2-(((4-chlorobenzoyl)oxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl 4-chlorobenzoate 
• 10310-21-1 2-Amino-6-chloropurin 
• 1294481-80-3 ((2R,3R,4R,5R)-3-((4-chlorobenzoyl)oxy)-4-fluoro-5-hydroxy-4-methyltetrahydrofuran-2-yl)methyl 4-chlorobenzoate 
• 1294481-79-0 ((2R,3R,4R) 3-(4-chlorobenzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl-4-chlorobenzoate 

Downstream Products

• 1199809-77-2 6-ethoxy-9-((2S,4aR,6R,7R,7aR)-7-fluoro-2-isopropoxy-7-methyl-2-oxo-tetrahydro-2λ(5)-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-2-ylamine 
• 1199809-32-9 PSI-938 
• 1199809-27-2 (2R,3R,4R,5R)-5-(2-amino-6-methoxy-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)-4-methyltetrahydrofuran-3-ol 
• 1199809-30-7 (2R,3R,4R,5R)-5-(2-amino-6-ethoxy-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)-4-methyltetrahydrofuran-3-ol 

Relevant articles and documents

The synthesis of hydroxyaminopurine nucleosied (by machine translation)

A compound or salt thereof having the following structure useful for the treatment of hepatitis C virus (HCV): wherein R 7 is C 1-6 alkyl or C 3-6 cycloalkyl and R 8 is -O(C 1-6 alkyl) or -O(C 3-6 cycloalkyl).

Stereoselective synthesis of PSI-352938: A β-D -2′-deoxy- 2′-α-fluoro-2′-β-C-methyl-3′,5′-cyclic phosphate nucleotide prodrug for the treatment of HCV

PSI-352938 is a novel 2′-deoxy-2′-α-fluoro-2′- β-C-methyl 3′,5′-cyclic phosphate nucleotide prodrug currently under investigation for the treatment of hepatitis C virus (HCV) infection. PSI-352938 demonstrated superior characteristics in vitro that include broad genotype coverage, superior resistance profile, and high levels of active triphosphate in vivo in the liver compared to our first and second generation nucleoside inhibitors of this class. Consequently, PSI-352938 was selected for further development and an efficient and scalable synthesis was sought to support clinical development. We report an improved, diastereoselective synthesis of a key 1′-β-nucleoside intermediate 13 via SN2 displacement of 1-α-bromo ribofuranose sugar 16 with the potassium salt of 6-chloro-2-amino purine and an efficient method to prepare cis-Rp cyclic phosphate (PSI-352938) in a highly stereoselective manner without any chromatographic purification. The 1-α-bromo sugar 16 was stereospecifically prepared from the corresponding 1-β-lactol in high yield under mild bromination conditions using CBr4/PPh3 (Appel reaction). The desired cis-Rp 3′,5′-cyclic phosphate construction was accomplished using isopropyl phosphorodichloridate readily obtained from POCl3 and isopropyl alcohol. The base combination of Et 3N/NMI was identified as a key factor for producing PSI-352938 as the major (>95%) diastereomer (cis-Rp) in high yield after the final cyclization step. The current route described in this article was successfully used to produce PSI-352938 on multikilogram scale.