89196-75-8

Basic information

• Product Name: 3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)phthalimide
• CAS NO: 89196-75-8
• Molecular Weight: 591.574
• Mol File: 89196-75-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)phthalimide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)phthalimide(89196-75-8)
• EPA Substance Registry System: 3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)phthalimide(89196-75-8)

Safety Data

• Hazardous Substances Data: 89196-75-8(Hazardous Substances Data)

Upstream product

• 86528-49-6 2-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)furan 

Relevant articles and documents

C-Nucleosides. 2. Synthesis of 3-(β-D-Ribofuranosyl)phthalimide

The synthesis of 3-(β-D-ribofuranosyl)phthalimide (19) from 2-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)furan (1) is described.One sequence started by aromatizing Diels-Alder-reaction adduct 2 to dimethyl 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)phthalate (3) with titanium tetrachloride-lithium aluminum hydride.Treatment of this with sodium hydroxide solution followed by dehydration with acetic anhydride and trifluoroacetic acid gave 3-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)phthalic anhydride (12).However, conversion of 12 into the phthalimide C-nucleoside was unsuccessful.The second sequence, which was brought to completion, made use of the adduct 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-7-oxabicyclohept-5-ene-2,3-dicarboximide (17) as the starting material.Treatment of this with sulfuric acid in dichloromethane yielded phthalimide 18, which on deblocking with sodium methoxide gave the desired phthalimide C-nucleoside 19.