171721-00-9

Basic information

• Product Name: 1,3,5-Tri-O-benzoyl-2-deoxy-2-fluoro-alpha-L-arabinofuranose
• Synonyms: 2-DEOXY-2-FLUORO-1,3,5-TRI-O-BENZOYL-L-RIBOFURANOSE;2-DEOXY-2-FLUORO-1,3,5-TRI-O-BZA-L-RIBOFURANOSE;1,3,5-Tri-O-benzoyl-2-deoxy-2-fluoro-a-L-arabinofuranose;1,3,5-Tri-O-benzoyl-2-deoxy-2-fluoro-alpha-L-arabinofuranose;(2S,3R,4S,5S)-5-((Benzoyloxy)Methyl)-3-fluorotetrahydrofuran-2,4-diyl dibenzoate;1,3,5-tri-benzoyl-2-Deoxy-2-fluoro-α-L-arabinofunose;2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-α-L-arabinofuranose
• CAS NO: 171721-00-9
• Molecular Formula: C₂₆H₂₁FO₇
• Molecular Weight: 464.44
• Mol File: 171721-00-9.mol

Chemical Properties

• Boiling Point: 584.13°C at 760 mmHg
• Flash Point: 295.665°C
• Appearance: /
• Density: 1.352g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.607
• CAS DataBase Reference: 1,3,5-Tri-O-benzoyl-2-deoxy-2-fluoro-alpha-L-arabinofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5-Tri-O-benzoyl-2-deoxy-2-fluoro-alpha-L-arabinofuranose(171721-00-9)
• EPA Substance Registry System: 1,3,5-Tri-O-benzoyl-2-deoxy-2-fluoro-alpha-L-arabinofuranose(171721-00-9)

Safety Data

• Hazardous Substances Data: 171721-00-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,3,5-Tri-O-benzoyl-2-deoxy-2-fluoro-alpha-L-arabinofuranose is used as a synthetic intermediate for the development of new pharmaceutical compounds. Its role in the synthesis of imidazole nucleoside derivatives and other related nucleosides contributes to the creation of novel therapeutic agents with potential applications in various medical conditions.
Used in Anticancer Applications:
Although not explicitly mentioned in the provided materials, given its role in the synthesis of nucleoside derivatives, 1,3,5-Tri-O-benzoyl-2-deoxy-2-fluoro-alpha-L-arabinofuranose may also have potential applications in the development of antineoplastic and alkylating agents. These agents are crucial in the treatment of various types of cancer, as they can inhibit tumor growth and proliferation.

InChI:InChI=1/C26H21FO7/c27-21-22(33-24(29)18-12-6-2-7-13-18)20(16-31-23(28)17-10-4-1-5-11-17)32-26(21)34-25(30)19-14-8-3-9-15-19/h1-15,20-22,26H,16H2/t20-,21+,22-,26-/m0/s1

Upstream product

• 171720-99-3 1,3,5-tri-O-benzoyl-2-O-(2-imidazolylsulfonyl)-α-L-ribofuranose 
• 171866-30-1 1,3,5-Tri-O-benzoyl-α-L-ribofuranose 
• 171866-28-7 1-O-methyl-2,3,5-tri-O-benzoyl-L-ribofuranose 
• 3080-30-6 1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose 
• 26685-74-5 1-O-benzyl-3,4-O-isopropylidene-β-L-ribopyranose 
• 65247-32-7 benzyl 3,4-O-(1-methylethylidene)-β-L-erythro-pent-2-ulosylpyranoside 
• 7296-55-1 L-arabinose 
• 87-72-9 L-ribose 
• 162491-62-5 (2S,3R,4S)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol 
• 7473-38-3 benzyl β-L-arabinopyranoside 
• 18403-22-0 (3aS,6S,7R,7aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol 
• 98-88-4 benzoyl chloride 
• 166411-40-1 5-O-benzoyl-1,2-O-isopropylidene-α-L-erythro-pentofuranose-3-ulose 
• 166411-39-8 5-O-benzoyl-1,2-O-isopropylidene-7α-L-xylofuranose 

Downstream Products

• 171866-29-8 1-bromo-2-deoxy-2-β-fluoro-3,5-di-O-benzoyl-α-L-arabinose 
• 371776-73-7 3,5-di-O-benzoyl-2-deoxy-2-fluoro-α-L-arabinofuranosyl azide 
• 371776-79-3 3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl azide 
• 371776-74-8 ethyl 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-α-L-arabinofuranosyl)-1,2,3-triazole-5-carboxylate 
• 371776-80-6 ethyl 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)-1,2,3-triazole-5-carboxylate 
• 371776-82-8 ethyl 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)-1,2,3-triazole-4-carboxylate 
• 371776-76-0 ethyl 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-α-L-arabinofuranosyl)-1,2,3-triazole-4-carboxylate 
• 163252-36-6 clevudine 
• 171721-03-2 1-(3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-β-L-arabinofuranosyl)thymine 
• 171721-03-2 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)thymine 
• 178687-95-1 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)-5-fluorocytosine 
• 178687-87-1 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)-5-fluorouracil 
• 178687-97-3 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)-5-chlorocytosine 
• 178687-89-3 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)-5-chlorouracil 

Relevant articles and documents

NOVEL 3′-DEOXY-3′-METHYLIDENE- -L-NUCLEOSIDES

The present invention includes novel 3′-deoxy-3′-methylidene-β-L-nucleosides, pharmaceutical composition comprising such compounds, as well as the methods to treat or to prevent viral infections and in particular HBV and/or HIV infections. In accordance with the present invention, there are provided compounds represented by Formula (I), wherein B is selected from A1 and A2;

IMPROVED PROCESS FOR THE PREPARATION OF CLEVUDINE AS ANTI-HBV AGENT

Disclosed herein is an improved method for preparing l -(2'-deoxy-2'- fluoro-beta-L-arabinofuranosyl) thymine (clevudine) useful as an anti-HBV (hepatitis B vims) agent. The method comprises an improved purification process of 2-O-imidazolylsulfonyl-l,3,5

Synthesis and Antiviral Activity of 2′-Deoxy-2′-fluoro-L-arabinofuranosyl 1,2,3-Triazole Derivatives

The title compounds were prepared by building up the triazole ring at the anomeric position via the glycosyl azides 5 a,b. The anomeric configurations of these nucleosides were assigned by using 1H, 13C and NOESY NMR spectroscopy. Th

A practical synthesis of L-FMAU from L-arabinose

A practical synthesis of 2'-deoxy-2'-fluoro-5-methyl-β-L- arabinofuranosyl uracil (14, L-FMAU) was developed from L-arabinose. L- Arabinose was convened to L-ribose 5, which was used for the synthesis of bromosugar 12 via 2,3,5-O-tribenzoyl-1-O-acetyl-β-L-ribofuranose 8, which was subjected to condensation with silylated thymine and the resulting protected L-FMAU 13 was deprotected to afford L-FMAU in 14 steps in 8% overall yield.

Structure-activity relationships of 1-(2-deoxy-2-fluoro-β-L-arabino- furanosyl)pyrimidine nucleosides as anti-hepatitis B virus agents

Since 2'-fluoro-5-methyl-β-L-arabinofuranosyluracil (L-FMAU) has been shown to be a potent anti-HBV agent in vitro, it was of interest to study the structure-activity relationships of related nucleosides. Thus, a series of 1- (2-deoxy-2-fluoro-β-L-arabinofuranosyl)pyrimidine nucleosides have been synthesized and evaluated for antiviral activity against HBV in 2.2.15 cells. For this study, L-ribose was initially used as the starting material. Due to the commercial cost of L-ribose, we have developed an efficient procedure for the preparation of L-ribose derivative 6. Starting from L-xylose, 6 was obtained in an excellent total yield (70%) through the pyridinium dichromate oxidation of the 3-OH group followed by stereoselective reduction with NaBH4. It was further converted to the 1,3,5-tri-O-benzoyl-2-deoxy-2- fluoro-α-L-arabinofuranose (10), which was then condensed with various 5- substituted pyrimidine bases to give the nucleosides. Among the compounds synthesized, the lead compound, L-FMAU (13), exhibited the most potent anti- HBV activity (EC50 0.1 μM). None of the other uracil derivatives showed significant anti-HBV activity up to 10 μM. Among the cytosine analogues, the cytosine (27) and 5-iodocytosine (35) derivatives showed moderately potent anti-HBV activity (EC50 1.4 and 5 μM, respectively). The cytotoxicity of these nucleoside analogues has also been assessed in 2.2.15 cells as well as CEM cells. None of these compounds displayed any toxicity up to 200 μM in 2.2.15 cells. Thus, compound 13 (L-FMAU), 27, and 35 showed a selectivity of over 2000, 140, and 40, respectively.