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

Uses

Methyl-5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside is an impurity of Capecitabine(C175650) which is an antineoplastic agent. Capecitabine is a prodrug of Doxifluridine (D556750).

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

• 70209-11-9 methyl (1R,2R,3R,4R)-2,3-O-isopropylidene-5-O-trifluoromethanesulfonyl-beta-D-ribofuranoside 
• 50-69-1 D-ribose 
• 532-20-7 D-Ribose 
• 77-76-9 2,2-dimethoxy-propane 
• 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 
• 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 
• 50610-99-6 1-O-methyl-2,3-O-isopropylidene-5-O-(methanesulfonyl)-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 
• 13039-75-3 5′-deoxyribose 
• 5531-24-8 L-5-deoxy-lyxose 
• 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.

Synthesizing method of capecitabine intermediate

The invention discloses a synthesizing method of a capecitabine intermediate and particularly relates to a synthesizing method of 1-methyl-5-deoxy-2, 3-O-isopropylidene-beta-D-furan riboside. The method includes: in N, N-dimethyl acetamide and in the presence of a boron reducing agent, using 1-methoxy-2, 3-O-isopropylidene-5-O-tosyl-beta-D-furan riboside to perform reduction reaction to obtain the 1-methyl-5-deoxy-2, 3-O-isopropylidene-beta-D-furan riboside. The synthesizing method has the advantages that the method is mild in reaction conditions, high in yield, environmentally friendly and suitable for industrial production, and the reaction solvent used by the method is easy to recycle and reusable.