171866-30-1

Basic information

• Product Name: 1,3,5-TRI-O-BENZOYL-ALPHA-L-RIBOFURANOSE
• Synonyms: 1,3,5-TRI-O-BENZOYL-ALPHA-L-RIBOFURANOSE;alpha-L-Ribofuranose 1,3,5-tribenzoate
• CAS NO: 171866-30-1
• Molecular Formula: C₂₆H₂₂O₈
• Molecular Weight: 462.45
• Mol File: 171866-30-1.mol

Chemical Properties

• Boiling Point: 629.6±55.0 °C(Predicted)
• Appearance: /
• Density: 1.37±0.1 g/cm3 (20 ºC 760 Torr)
• PKA: 12.35±0.70(Predicted)
• CAS DataBase Reference: 1,3,5-TRI-O-BENZOYL-ALPHA-L-RIBOFURANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5-TRI-O-BENZOYL-ALPHA-L-RIBOFURANOSE(171866-30-1)
• EPA Substance Registry System: 1,3,5-TRI-O-BENZOYL-ALPHA-L-RIBOFURANOSE(171866-30-1)

Safety Data

• Hazardous Substances Data: 171866-30-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1,3,5-TRI-O-BENZOYL-ALPHA-L-RIBOFURANOSE serves as a crucial intermediate in organic synthesis, where it is used as a building block for the assembly of more complex organic molecules. Its unique structure allows for the development of novel compounds with potential applications across various industries.
Used in Pharmaceutical Research and Development:
In the pharmaceutical industry, 1,3,5-TRI-O-BENZOYL-ALPHA-L-RIBOFURANOSE is utilized as a key component in the design and synthesis of new drug candidates. Its properties make it a promising starting point for the creation of innovative medications, particularly those targeting challenging diseases.
Used in Biotechnology Applications:
1,3,5-TRI-O-BENZOYL-ALPHA-L-RIBOFURANOSE also finds use in the biotechnology field, where it can be employed in the development of new biological products. Its role in the synthesis of complex molecules makes it a valuable asset in advancing biotechnological solutions for various applications.
Used in Academic Research:
1,3,5-TRI-O-BENZOYL-ALPHA-L-RIBOFURANOSE is also widely used in academic research settings, where scientists explore its properties and potential interactions with other molecules. This research can lead to a better understanding of chemical reactions and the development of new methodologies in organic chemistry.

Upstream product

• 3080-30-6 1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose 
• 171866-28-7 1-O-methyl-2,3,5-tri-O-benzoyl-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 
• 171721-12-3 1,2-di-O-isopropylidene-3,5-di-O-benzoyl-α-L-ribofuranose 
• 172949-42-7 (3aS,5S,6S,6aS)-5-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxol-6-ol 

Downstream Products

• 171720-99-3 1,3,5-tri-O-benzoyl-2-O-(2-imidazolylsulfonyl)-α-L-ribofuranose 
• 163252-36-6 clevudine 
• 171721-03-2 1-(3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-β-L-arabinofuranosyl)thymine 
• 339091-15-5 2-O-Acetyl-1,3,5-tri-O-benzoyl-α-L-ribofuranose 
• 339091-18-8 L-2-O-[(trifluoromethyl)sulfonyl]-1,3,5-tri-O-benzoyl-α-D-ribofuranose 
• 371776-72-6 1,3,5-tri-O-benzoyl-2-O-imidazolyl-sulfonyl-α-L-ribofuranose 
• 1312300-53-0 C₂₃H₁₉FN₂O₇ 
• 7473-41-8 1,3,5-tri-O-benzoyl-α-L-arabinofuranose 
• 38791-39-8 C₂₇H₂₄O₈ 
• 1092652-27-1 2'-deoxy-2'-[18F]fluoro-3',5'-di-O-benzoyl-5-methyl-1β-L-arabinofuranosyluracil 
• 1092652-25-9 2-deoxy-2-fluoro-1,3,5-tri-O-benzoyl-α-L-arabinofuranose 
• 1092652-26-0 1-bromo-2-deoxy-2-[18F]fluoro-3,5-di-O-benzoyl-α-L-arabinofuranose 
• 171721-05-4 N⁴-benzoyl-1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)-5-iodocytosine 
• 178688-01-2 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)-5-[2-(trimethylsilyl)acetylenyl]uracil 

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;

2'-deoxy-L-nucleosides

This invention provides processes for the preparation of compounds having the structure: wherein X and Y are same or different, and H, OH, OR, SH, SR, NH2, NHR′, or NR′R″Z is H, F, Cl, Br, I, CN, or NH2. R is hydrogen, halogen, lower alkyl of C1-C6 or aralkyl, NO2, NH2, NHR′, NR′R″, OH, OR, SH, SR, CN, CONH2, CSNH2, CO2H, CO2R′, CH2CO2H, CH2CO2R′, CH═CHR, CH2CH═CHR, or C═CR. R′ and R″ are same or different, and lower alkyl of C1-C6. R13 is hydrogen, alkyl, acyl, phosphate (monophosphate, diphosphate, triphosphate, or stabilized phosphate) or silyl; and

PROCESS FOR THE PREPARATION OF 2'- FLUORO-5-METHYL-BETA-L-ARABINO- FURANOSYLURIDINE

The present invention relates to a novel and improved process for preparing 2′-fluoro-5-methyl-β-L-arabinofuranosyluridine represented by formula (1) which shows anti-viral activity, especially potent anti-viral activity against hepatitis B-virus and Epstein-Barr virus:

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.