136035-14-8

Basic information

• Product Name: Amino nucleoside
• Synonyms: 1-(3-Amino-2,3,6-trideoxy-.alpha.-L-arabino-hexofuranosyl)thymine;2,4(1H,3H)-Pyrimidinedione, 1-(3-amino-2,3,6-trideoxy-.alpha.-L-arabino-hexofuranosyl)-5-methyl-;Aids002987;Aids-002987
• CAS NO: 136035-14-8
• Molecular Formula: C11H17N3O4
• Molecular Weight: 255.27038
• Mol File: 136035-14-8.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Density: 1.33g/cm³
• Refractive Index: 1.563
• CAS DataBase Reference: Amino nucleoside(CAS DataBase Reference)
• NIST Chemistry Reference: Amino nucleoside(136035-14-8)
• EPA Substance Registry System: Amino nucleoside(136035-14-8)

Safety Data

• Hazardous Substances Data: 136035-14-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H17N3O4/c1-5-4-14(11(17)13-10(5)16)8-3-7(12)9(18-8)6(2)15/h4,6-9,15H,3,12H2,1-2H3,(H,13,16,17)/t6-,7-,8+,9-/m0/s1

Upstream product

• 34819-86-8 3,4-di-O-acetyl-6-deoxy-L-glucal 
• 136035-08-0 1,5-di-O-acetyl-2,3,6-trideoxy-3-phthalimido-α-L-arabino-hexofuranose 
• 136035-06-8 5-O-acetyl-2,3,6-trideoxy-3-phthalimido-L-arabino-hexofuranose 
• 101223-02-3 (E)-4-O-acetyl-2,3,6-trideoxy-aldehydo-L-erythro-hex-2-enose 
• 136035-11-5 1-(5-O-acetyl-3-phthalimido-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.