34339-66-7

Upstream product

• 34724-16-8 1,2;3,3'-di-O-isopropylidene-3-C-(hydroxymethyl)-α-D-erythrofuranose 
• 34693-28-2 (3aR,6aS)-2,2-dimethyl-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-6(5H)-one 
• 14048-35-2 (-)-(3aR,6S,6aR)-6-hydroxymethyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol 
• 100-39-0 benzyl bromide 
• 34693-27-1 (3aR,6S,6aR)-6-hydroxy-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxole 
• 14048-38-5 (3aR,6aR)-2,2-dimethyl-6-methylenetetrahydrofuro[2,3-d][1,3]dioxole 

Downstream Products

• 28440-12-2 1'-(adenin-9-yl)-α-D-apio-L-furanose 
• 681811-48-3 (-)-(3aR,6R,6aR)-6-benzyloxymethyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole 
• 1610459-61-4 1,2-di-O-acetyl-3-deoxy-5-(O-benzyl)-α-D-apio-L-furanose 
• 1610459-60-3 1,2-di-O-acetyl-3-deoxy-5-(O-benzyl)-β-D-apio-L-furanose 
• 1610459-62-5 1-O-methyl-2-O-acetyl-3-deoxy-5-(O-benzyl)-β-D-apio-L-furanose 
• 1610459-64-7 1,2,3-tri-(O-acetyl)-5-(O-benzyl)-β-D-apio-L-furanose 
• 1610459-66-9 1,2-di-O-acetyl-3-deoxy-5-(O-benzyl)-α-D-apio-D-furanose 
• 1610459-67-0 1,2-di-O-acetyl-3-deoxy-5-(O-benzyl)-β-D-apio-D-furanose 
• 1610459-68-1 1'-(thymin-1-yl)-2'-O-acetyl-3'-deoxy-5'-O-benzyl-α-D-apio-L-furanose 
• 1610459-69-2 1'-(thymin-1-yl)-2'-O-acetyl-3'-deoxy-5'-O-benzyl-β-D-apio-L-furanose 
• 1610459-70-5 1'-(N⁶-benzoyladenin-9-yl)-2'-O-acetyl-3'-deoxy-5'-O-benzyl-α-D-apio-L-furanose 
• 1610459-73-8 1'-(thymin-1-yl)-2',3'-di(O-acetyl)-5'-O-benzyl-α-D-apio-L-furanose 
• 1610459-74-9 1'-(N⁶-benzoyladenin-9-yl)-2',3'-di(O-acetyl)-5'-O-benzyl-α-D-apio-L-furanose 
• 1610459-75-0 1'-(N⁶-benzoyladenin-9-yl)-2'-(O-trimethylsilyl)-3'-(O-acetyl)-5'-O-benzyl-α-D-apio-L-furanose 

Relevant academic research and scientific papers

Synthesis of an apionucleoside family and discovery of a prodrug with anti-HIV activity

We report the synthesis of a family of d- and l-furano-d-apionucleosides, their 3'-deoxy, as well as their 2',3'-dideoxy analogues with thymine and adenine nucleobases. Single carbon homologation of 1,2-O-isopropylidene-d- glycero-tetrafuranos-3-ulose (15) and optimized glycosylation conditions involving microwave irradiation were key to the successful synthesis of the target compounds. While all target nucleosides failed to show significant antiviral activity, we demonstrated that the triphosphate of 2',3'-deoxy-d-apio-d-furanoadenosine (1), in contrast to that of its d-apio-l-furanose epimer 2, was readily incorporated into a DNA template by HIV reverse transcriptase to act as a DNA chain terminator. This led us to convert adenine derivative 1 into two phosphoramidate prodrugs. ProTide 9b was found active against HIV-1 and HIV-2 (EC50 = 0.5-1.5 μM), indicating that the lack of activity of the parent nucleoside, and possibly also other members of the d-apio-d-furanose nucleoside family must be sought in the inefficient cellular conversion to the monophosphate.

Synthesis of D- and L-apio nucleoside analogues with 2′-hydroxyl group as potential anti-HIV agents

The present work describes the asymmetric synthesis of D- and L-apio-2′,3′-dideoxynucleoside analogues, 4 and 5 with 2′-hydroxyl group via a common intermediate 9, starting from D-galactose. Stereoselective dihydroxylation and deoxygenation through radica

Synthesis of Bis-γ-Butyrolactones Containing Conformationally Constrained (S)- and (R)-Diacylglycerol Structures

The synthesis of two sets of rigid diacylglycerol (DAG) analogues with either the (S)-DAG or (R)-DAG enantiomer embedded into a bis-γ-butyrolactone template was accomplished stereoselectively from di-O-isopropylidene-α-D-apiose.The key step in both synthe

Synthesis of two rigid diacylglycerol analogues having a bis-butyrolactone skeleton

The stereoselective synthesis of two rigid diacylglycerol analogues starting from protected D-apio-L-furanose (apiose) is described. The construction of the desired bis-butyrolactone bicyclic structure was accomplished via an intramolecular radical cycliz