23202-81-5

Basic information

• Product Name: Methyl-5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranoside
• Synonyms: methyl 5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranoside;5-Deoxy-2,3-O-isopropylidene-D-ribofuranoside;1-O-Methyl-2,3-O-isopropylidene-5-Deoxy-β-D-Ribose;B-D-RIBOFURANOSIDE,;(R)-1-((4R,5S)-5-(methoxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol;1-O-Methyl-2,3-O-isopropylidene-5-Deoxy-beta-D-ribose;Methyl 2-O,3-O-(1-methylethylidene)-5-deoxy-β-D-ribofuranoside;Methyl 2-O,3-O-isopropylidene-5-deoxy-β-D-ribofuranoside
• CAS NO: 23202-81-5
• Molecular Formula: C₉H₁₆O₄
• Molecular Weight: 188.221
• EINECS: 245-485-1
• Mol File: 23202-81-5.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 225.623 °C at 760 mmHg
• Flash Point: 88.612 °C
• Appearance: /
• Density: 1.12 g/cm³
• Vapor Pressure: 0.128mmHg at 25°C
• Refractive Index: 1.465
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Methyl-5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl-5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranoside(23202-81-5)
• EPA Substance Registry System: Methyl-5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranoside(23202-81-5)

Safety Data

• Hazardous Substances Data: 23202-81-5(Hazardous Substances Data)

Usage

Description

Methyl-5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranoside is a chemical compound that serves as an impurity in the production of Capecitabine (C175650), an antineoplastic agent. Methyl-5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranoside is derived from the synthesis process of Capecitabine, which is a prodrug of Doxifluridine (D556750). Methyl-5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranoside is characterized by its unique chemical structure and properties, which differentiate it from the active pharmaceutical ingredient.

Uses

Used in Pharmaceutical Industry:
Methyl-5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranoside is used as an impurity in the production of Capecitabine, an antineoplastic agent. Its presence in the synthesis process is crucial for the development of the final drug product, which is used for the treatment of various types of cancer. The compound plays a significant role in the pharmaceutical industry due to its association with the production of Capecitabine.
Used in Research and Development:
Methyl-5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranoside is also utilized in research and development for the study of its chemical properties and potential applications. Scientists and researchers investigate the compound's interactions with other molecules and its potential use in the development of new drugs or drug delivery systems.
Used in Quality Control and Analysis:
In the pharmaceutical industry, Methyl-5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranoside is used for quality control and analysis purposes. Its presence in the synthesis process of Capecitabine is monitored to ensure the purity and efficacy of the final drug product. The compound serves as a critical parameter in the quality assurance process, helping to maintain the safety and effectiveness of the antineoplastic agent.

InChI:InChI=1/C9H16O4/c1-5-6-7(8(10-4)11-5)13-9(2,3)12-6/h5-8H,1-4H3/t5-,6-,7-,8-/m1/s1

Upstream product

• 4099-85-8 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 4137-56-8 methyl 2,3-O-isopropylidene-5-O-p-tolylsulfonyl-β-D-ribofuranoside 
• 50-69-1 D-ribose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 917028-22-9 1,2-O-isopropylidene-5-O-methylsulphonyl-3-O-(methoxyethoxymethyl)-α-D-ribofuranose 
• 1009735-34-5 1,2;5,6-di-O-isopropylidene-3-O-(methoxyethoxymethyl)-α-D-allofuranose 
• 1009735-30-1 1,2-O-isopropylidene-3-O-(methoxyethoxymethyl)-α-D-allofuranose 
• 923056-82-0 1,2-O-isopropylidene-3-O-(methoxyethoxymethyl)-α-D-ribofuranose 
• 14686-89-6 (1,2:5,6)-di-O-isopropylidene-D-gulose 
• 36468-53-8 β-D-ribofuranose 
• 70209-11-9 methyl (1R,2R,3R,4R)-2,3-O-isopropylidene-5-O-trifluoromethanesulfonyl-beta-D-ribofuranoside 
• 50610-99-6 1-O-methyl-2,3-O-isopropylidene-5-O-(methanesulfonyl)-β-D-ribofuranoside 
• 38838-05-0 1-O-methyl-2,3-O-isopropylidene-5-bromo-5-deoxy-β-D-ribofuranoside 
• 33985-42-1 Methyl 5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranoside 

Downstream Products

• 27821-07-4 1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose 
• 158112-55-1 5-O-deoxy-D-ribofuranose 
• 5531-24-8 L-5-deoxy-lyxose 
• 13039-75-3 5′-deoxyribose 
• 162204-20-8 N¹-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N⁴-(pentyloxycarbonyl)cytosine 
• 161599-46-8 (2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate 
• 279673-09-5 (2R,3R,4S,5R)-5-methyltetrahydrofuran-2,3,4-triol 
• 154361-50-9 capecitabine 

Relevant articles and documents

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A Novel Method for the Deoxygenation of Acetylated Sugars

The conversion of acetylated sugars 1 to deoxy sugars 2 by the action of triphenylsilane under homolytic conditions is reported.Both furanoses and pyranoses bearing an acetylated primary or seondary alcohol are effectively deoxygenated.

Synthesis of 1,2,3-tri-O-acetyl-5-deoxy-D-ribofuranose from D-ribose

A practical route towards the synthesis of 1,2,3-tri-O-acetyl-5-deoxy-D-ribofuranose from D-ribose is described. The key steps include deoxygenation of methyl 2,3-O-isopropylidene-5-O-sulfonyloxy-β-D-ribofuranoside by reductive displacement employing hydride reagents. Subsequent total hydrolysis followed by acetylation led to the title compound in 56% overall yield from D-ribose. The sequence is simple, inexpensive, high yielding and clearly suitable for multi-gram preparations.

Computer Modelling and Synthesis of Deoxy and Monohydroxy Analogues of a Ribitylaminouracil Bacterial Metabolite that Potently Activates Human T Cells

5-(2-Oxopropylideneamino)-6-d-ribitylaminouracil (5-OP-RU) is a natural product formed during bacterial synthesis of vitamin B2. It potently activates mucosal associated invariant T (MAIT) cells and has immunomodulatory, inflammatory, and anticancer properties. This highly polar and unstable compound forms a remarkably stable Schiff base with a lysine residue in major histocompatibility complex class I–related protein (MR1) expressed in antigen-presenting cells. Inspired by the importance of the ribityl moiety of 5-OP-RU for binding to both MR1 and the T cell receptor (TCR) on MAIT cells, each OH was removed in silico. DFT calculations and MD simulations revealed a very stable hydrogen bond between the C3′?OH and uracil N1H, which profoundly restricts flexibility and positioning of each ribityl-OH, potentially impacting their interactions with MR1 and TCR. By using deoxygenation strategies and kinetically controlled imine formation, four monodeoxyribityl and four monohydroxyalkyl analogues of 5-OP-RU were synthesised as new tools for probing T cell activation mechanisms.

Synthesis of Nucleosides through Direct Glycosylation of Nucleobases with 5-O-Monoprotected or 5-Modified Ribose: Improved Protocol, Scope, and Mechanism

Simplifying access to synthetic nucleosides is of interest due to their widespread use as biochemical or anticancer and antiviral agents. Herein, a direct stereoselective method to access an expansive range of both natural and synthetic nucleosides up to a gram scale, through direct glycosylation of nucleobases with 5-O-tritylribose and other C5-modified ribose derivatives, is discussed in detail. The reaction proceeds through nucleophilic epoxide ring opening of an in situ formed 1,2-anhydrosugar (termed “anhydrose”) under modified Mitsunobu reaction conditions. The scope of the reaction in the synthesis of diverse nucleosides and other 1-substituted riboside derivatives is described. In addition, a mechanistic insight into the formation of this key glycosyl donor intermediate is provided.