301826-41-5

Upstream product

• 238096-55-4 N-(2-((1-trimethylsilyl)oxy)pyrimidin-4-yl)benzamide 
• 301826-40-4 1-O-acetyl-3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-D-glycero-tetrofuranose 
• 220569-96-0 ethyl (R)-3-benzyloxymethyl-3-methyl-4-oxobutyrate 
• 220569-97-1 3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-D-glycero-tetrofuranose 
• 26661-13-2 4-N-benzoylcytosine 

Relevant academic research and scientific papers

Synthesis of novel 3'-C-methyl-apionucleosides: An asymmetric construction of a quaternary carbon by claisen rearrangement

The synthesis of 2,3-dideoxy-3-C-(hydroxymethyl)-3-C-glycero-tetrofuranosyl nucleosides was accomplished in high enatiomeric purity (98.5% ee) via [3,3]-sigmatropic Claisen rearrangement of (E)(S)-5-benzyloxy-1-tert-butyldimethylsilanyloxy-4-methyl-pent-3 -en-2-ol prepared from 2,3-O-isopropylidene-D-glyceraldehyde. The synthesized nucleosides were assayed against human immunodeficiency virus (HIV) and hepatitis B virus in human peripheral blood mononuclear (PBM) and 2.2.15 cells, respectively. 6-Amino-9-[2,3-dideoxy-3-C-(hydroxymethyl)-3-C-methyl-β-D-glycer o-tetrofuranosyl]-2-fluoropurine shows moderate antiviral activity (EC50 = 2.55 μM) against HIV-1 strains and 6-amino-9-[3-deoxy-3-C-(hydroxymethyl)-3-methyl-α-D-glycero-tetr ofuranosyl]-2-fluoropurine exhibits potent anti-HIV activity EC50 = 0.073 μM) with significant cytotoxity (IC50 = 1.0 μM). (C) 2000 Elsevier Science Ltd.