52554-28-6

Basic information

• Product Name: Methyl 2,3,5-tri-O-acetyl-D-ribofuranoside
• Synonyms: Methyl 2,3,5-tri-O-acetyl-D-ribofuranoside;(2R,3R,4R)-2-(acetoxymethyl)-5-methoxytetrahydrofuran-3,4-diyl diacetate
• CAS NO: 52554-28-6
• Molecular Formula: C₁₂H₁₈O₈
• Molecular Weight: 290.27
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 52554-28-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 355.4 °C at 760 mmHg
• Flash Point: 154.6 °C
• Appearance: /
• Density: 1.24 g/cm³
• Vapor Pressure: 3.15E-05mmHg at 25°C
• Refractive Index: 1.466
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Dicholoromethane, Methanol
• CAS DataBase Reference: Methyl 2,3,5-tri-O-acetyl-D-ribofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2,3,5-tri-O-acetyl-D-ribofuranoside(52554-28-6)
• EPA Substance Registry System: Methyl 2,3,5-tri-O-acetyl-D-ribofuranoside(52554-28-6)

Safety Data

• Hazardous Substances Data: 52554-28-6(Hazardous Substances Data)

Usage

Chemical Properties

Clear Oil

Uses

Methyl 2,3,5-Tri-O-acetyl-D-ribofuranoside (cas# 52554-28-6) is a compound useful in organic synthesis.

InChI:InChI=1/C12H18O8/c1-6(13)17-5-9-10(18-7(2)14)11(19-8(3)15)12(16-4)20-9/h9-12H,5H2,1-4H3/t9-,10-,11-,12?/m1/s1

Upstream product

• 10257-32-6 D-ribose 
• 1824-96-0 methyl ribofuranoside 
• 108-24-7 acetic anhydride 
• 6979-94-8 2',3',5'-tri-O-acetyl-guanosine 
• 161925-21-9 3-(methoxymethyl)-3-phenyldioxetane 

Downstream Products

• 13035-61-5 1,2,3,5-tetraacetylribose 
• 50730-26-2 tetra-O-acetyl-D-ribofuranose 
• 28708-32-9 1,2,3,5-tetra-O-acetyl-D-ribofuranose 

Relevant articles and documents

Highly Stereoselective Glycosylation Reactions of Furanoside Derivatives via Rhenium (V) Catalysis

A novel approach for the formation of anomeric carbon-functionalized furanoside systems was accomplished through the employment of an oxo-rhenium catalyst. The transformation boasts a broad range of nucleophiles including allylsilanes, enol ethers, and aromatics in addition to sulfur, nitrogen, and hydride donors, able to react with an oxocarbenium ion intermediate derived from furanosidic structures. The excellent stereoselectivities observed followed the Woerpel model, ultimately providing 1,3-cis-1,4-trans systems. In the case of electron-rich aromatic nucleophiles, an equilibration occurs at the anomeric center with the selective formation of 1,3-trans-1,4-cis systems. This anomalous result was rationalized through density functional theory calculations. Different oxocarbenium ions such as those derived from dihydroisobenzofuran, pyrrolidine, and oxazolidine heterocycles can also be used as a substrate for the oxo-Re-mediated allylation reaction.

Process and intermediate compounds for the preparation of pyrrolidines

Processes for the preparation of pyrrolidones (7 and 8) and pyrrolidines (9 and 10) from tri-O-acetyl-D-erythro-4-pentulosonic acid esters are described. The compounds are aza sugar analogs of D-ribofuranoside and are intermediates to drugs which regulate nucleoside and nucleic acid synthesis.