136035-11-5

Basic information

• Product Name: 1-[5-O-acetyl-2,3,6-trideoxy-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-alpha-L-arabino-hexofuranosyl]-5-methylpyrimidine-2,4(1H,3H)-dione
• CAS NO: 136035-11-5
• Molecular Formula: C₂₁H₂₁N₃O₇
• Molecular Weight: 427.4073
• Mol File: 136035-11-5.mol
• Article Data: 1

Chemical Properties

• Density: 1.426g/cm³
• Refractive Index: 1.61
• CAS DataBase Reference: 1-[5-O-acetyl-2,3,6-trideoxy-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-alpha-L-arabino-hexofuranosyl]-5-methylpyrimidine-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[5-O-acetyl-2,3,6-trideoxy-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-alpha-L-arabino-hexofuranosyl]-5-methylpyrimidine-2,4(1H,3H)-dione(136035-11-5)
• EPA Substance Registry System: 1-[5-O-acetyl-2,3,6-trideoxy-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-alpha-L-arabino-hexofuranosyl]-5-methylpyrimidine-2,4(1H,3H)-dione(136035-11-5)

Safety Data

• Hazardous Substances Data: 136035-11-5(Hazardous Substances Data)

Upstream product

• 136035-08-0 1,5-di-O-acetyl-2,3,6-trideoxy-3-phthalimido-α-L-arabino-hexofuranose 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 101223-02-3 (E)-4-O-acetyl-2,3,6-trideoxy-aldehydo-L-erythro-hex-2-enose 
• 136035-06-8 5-O-acetyl-2,3,6-trideoxy-3-phthalimido-L-arabino-hexofuranose 
• 34819-86-8 3,4-di-O-acetyl-6-deoxy-L-glucal 

Downstream Products

• 136035-14-8 1-(3-amino-2,3,6-trideoxy-α-L-arabino-hexofuranosyl)thymine 

Relevant articles and documents

Synthesis and evaluation of antiviral activity of L-acosamine and L-ristosamine nucleosides of furanose configuration.

Mercuric-catalyzed hydrolysis of acetylated L-rhamnal 1 gives an alpha,beta-unsaturated aldehyde 2. 1,4-Addition of DBU-phthalimide salt with concomitant acetyl shift resulted in L-ribo and L-arabino isomers of 5-O-acetyl-2,3,6-trideoxy-3-phthalimido-hexofuranose 3 and 4. After acetylation at the anomeric center, coupling with silylated thymine resulted in three new nucleosides, with L-acosamine and L-ristosamine of furanose configuration as the carbohydrate moiety. The target compounds have been evaluated for their antiviral activity against HIV and HSV-1.