55725-85-4

Basic information

• Product Name: Methyl 2,3,5-tri-O-benzyl-beta-D-ribofuranoside
• Synonyms: Methyl2,3,5-tri-O-benzyl-β-D-ribofuranoside;1-methoxy-2,3,5-tri-benzoyl-D-ribose;Methyl 2,3,5-tri-O-benzyl-beta-D-ribofuranoside;(2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-methoxytetrahydrofuran;Methyl 2,3,5-Tris-O-(phenylMethyl)-β-D-ribofuranoside;2-methoxy-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolane
• CAS NO: 55725-85-4
• Molecular Formula: C₂₇H₃₀O₅
• Molecular Weight: 434.52
• Product Categories: Carbohydrates & Derivatives
• Mol File: 55725-85-4.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 552.589 °C at 760 mmHg
• Flash Point: 217.358 °C
• Appearance: /
• Density: 1.174g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.587
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Ethyl Acetate
• CAS DataBase Reference: Methyl 2,3,5-tri-O-benzyl-beta-D-ribofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2,3,5-tri-O-benzyl-beta-D-ribofuranoside(55725-85-4)
• EPA Substance Registry System: Methyl 2,3,5-tri-O-benzyl-beta-D-ribofuranoside(55725-85-4)

Safety Data

• Hazardous Substances Data: 55725-85-4(Hazardous Substances Data)

Usage

Description

Methyl 2,3,5-tri-O-benzyl-beta-D-ribofuranoside is a synthetic compound that is utilized in the field of organic synthesis. It is characterized by its yellow oil appearance and is known for its unique chemical properties that make it a valuable component in various chemical reactions and processes.

Uses

Used in Organic Synthesis:
Methyl 2,3,5-tri-O-benzyl-beta-D-ribofuranoside is used as a key intermediate in organic synthesis for the development of various complex organic molecules. Its unique structure allows it to participate in a wide range of chemical reactions, making it a versatile building block for creating novel compounds with potential applications in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl 2,3,5-tri-O-benzyl-beta-D-ribofuranoside is used as a starting material for the synthesis of bioactive compounds, including potential drug candidates. Its ability to be modified and functionalized makes it a valuable asset in the development of new medications with improved efficacy and reduced side effects.
Used in Chemical Research:
Methyl 2,3,5-tri-O-benzyl-beta-D-ribofuranoside is also used in academic and industrial research settings as a model compound for studying various aspects of organic chemistry, such as reaction mechanisms, stereochemistry, and the development of new synthetic methods. Its unique properties make it an ideal candidate for probing the limits of chemical reactivity and understanding the underlying principles governing complex chemical transformations.

InChI:InChI=1/C27H30O5/c1-28-27-26(31-19-23-15-9-4-10-16-23)25(30-18-22-13-7-3-8-14-22)24(32-27)20-29-17-21-11-5-2-6-12-21/h2-16,24-27H,17-20H2,1H3/t24-,25-,26-,27-/m1/s1

Upstream product

• 67737-48-8 methyl 5-benzyloxy-β-D-ribofuranoside 
• 100-44-7 benzyl chloride 
• 16838-89-4 2,3,5-tri-O-benzyl-D-ribofuranose 
• 4356-80-3 methyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside 
• 1824-96-0 methyl ribofuranoside 
• 100-39-0 benzyl bromide 
• 86883-41-2 2,3,5-tri-O-benzyl-α-D-ribofuranosyl fluoride 
• 33019-63-5 (2R,3R,4R,5R)-2-benzyloxymethyl-3,4-isopropylidenedioxy-5-methoxytetrahydrofuran 
• 191543-71-2 methyl 3,5-di-O-benzyl-α-D-ribofuranoside 
• 1825-61-2 Trimethylmethoxysilane 
• 96-36-6 methyl phosphite 
• 67-56-1 methanol 
• 86883-42-3 2,3,5-tris-O-(phenylmethyl)-β-D-ribofuranosyl fluoride 

Downstream Products

• 79083-29-7 (2R,3R,4R,5S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran 
• 79064-00-9 (2R,3R,4S)-1,3,4-Tris-benzyloxy-5-methoxy-hexan-2-ol 
• 491-19-0 1,4-anhydro-D-ribitol 
• 191543-71-2 methyl 3,5-di-O-benzyl-α-D-ribofuranoside 
• 1428321-46-3 (1R,2R,3R,4R)-2,3,5-tris(benzyloxy)-1-methoxy-1-(phenylthio)pentan-4-ol 
• 93836-22-7 4,7-anhydro-5,6,8-tri-O-benzyl-1,2,3-trideoxy-D-altro-oct-1-enitol 
• 1330085-36-3 3-(2,3,5-tri-O-benzyl-α-D-ribofuranosyl)-1-propyne 
• 1333119-43-9 C₃₆H₄₆O₅ 
• 1333119-42-8 4-penten-1-yl 2,3,5-tri-O-benzyl-β-D-ribofuranoside 
• 92414-06-7 cyclohexyl 2,3,5-tri-O-benzyl-β-D-ribofuranoside 
• 92414-08-9 cyclohexyl 2,3,5-tri-O-benzyl-α-D-ribofuranoside 
• 149118-07-0 (2R,3R,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-phenylsulfanyl-tetrahydro-furan 

Relevant articles and documents

Anodic coupling reactions and the synthesis of C-glycosides

A convenient, two-step procedure has been developed for converting sugar derivatives into C-glycosides containing a masked aldehyde functional group. The chemistry takes advantage of an anodic coupling reaction between an electron-rich olefin and an alcohol. The sequence works for the formation of both furanose and pyranose derivatives if less polarized vinyl sulfide derived radical cation intermediates are used. With more polarized enol ether derived radical cations, the cyclizations work best for the formation of furanose derivatives where the rate of five-membered ring formation precludes elimination reactions triggered by the radical cation.

Synthesis of β-D-ribofuranosyl-(1→3)-α-L-rhamnopyranose by in situ activating glycosylation using 1-OH sugar derivative and Me3SiBr-CoBr2-Bu4NBr-molecular sieves 4A system

Β-D-Ribofuranosyl-(1→3)-α-L-rhamnopyranosyl-(1→3)- L-rhamnopyranose, the trisaccharide repeating unit of the C. freundii O28, 1c O-specific polysaccharide, was synthesized using in situ activating glycosylation of the 1-OH sugar derivatives and a reagent mixture of trimethylsilyl bromide, cobalt(II) bromide, tetrabutylammonium bromide, and molecular sieves 4A. Regioselective tritylation was useful for synthesizing the 3-OH derivatives of methyl, allyl, and benzyl α-L-rhamnosides.

An Efficient Method for the Stereoselective Synthesis of β-D- and α-D-Ribofuranosides from 2,3,5-Tri-O-benzyl-D-ribofuranose by the Use of oxotitanium and Trifluoromethanesulfonic Anhydride

β-D-Ribofuranoside are stereoselectively synthesized in high yields directly from 2,3,5-tri-O-benzyl-D-ribofuranose and trimethylsilylated nucleophiles by the use of oxotitanium and trifluoromethanesulfonic anhydride, while α-D-ribof