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

Chemical Properties

Yellow Oil

Uses

Methyl 2,3,5-Tri-O-benzyl-β-D-ribofuranoside (cas# 55725-85-4) is a compound useful in organic synthesis.

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

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

Downstream Products

• 191543-71-2 methyl 3,5-di-O-benzyl-α-D-ribofuranoside 
• 1333119-42-8 4-penten-1-yl 2,3,5-tri-O-benzyl-β-D-ribofuranoside 
• 1333119-43-9 C₃₆H₄₆O₅ 
• 1428321-46-3 (1R,2R,3R,4R)-2,3,5-tris(benzyloxy)-1-methoxy-1-(phenylthio)pentan-4-ol 
• 149118-07-0 (2R,3R,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-phenylsulfanyl-tetrahydro-furan 
• 491-19-0 1,4-anhydro-D-ribitol 
• 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 
• 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 
• 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 

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