259877-34-4

Basic information

• Product Name: (2R,3S,5R)-5-allyl-3-(benzyloxy)-2-((benzyloxy)methyl)-tetrahydrofuran
• Synonyms: (2R,3S,5R)-5-allyl-3-(benzyloxy)-2-((benzyloxy)methyl)-tetrahydrofuran
• CAS NO: 259877-34-4
• Molecular Weight: 338.447
• Mol File: 259877-34-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2R,3S,5R)-5-allyl-3-(benzyloxy)-2-((benzyloxy)methyl)-tetrahydrofuran(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,5R)-5-allyl-3-(benzyloxy)-2-((benzyloxy)methyl)-tetrahydrofuran(259877-34-4)
• EPA Substance Registry System: (2R,3S,5R)-5-allyl-3-(benzyloxy)-2-((benzyloxy)methyl)-tetrahydrofuran(259877-34-4)

Safety Data

• Hazardous Substances Data: 259877-34-4(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 51255-17-5 1-O-methyl-2-deoxy-D-ribofuranoside 
• 6160-49-2 1-O-acetyl-3,5-di-O-benzyl-2-deoxy-D-erythro-pentofuranose 
• 762-72-1 allyl-trimethyl-silane 
• 132487-16-2 methyl 3,5-di-O-benzyl-2-deoxy-D-ribofuranoside 
• 6160-50-5 3,5-di-O-benzyl-2-deoxy-D-ribofuranose 
• 1200119-30-7 C₂₂H₂₈O₄ 

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.