238096-55-4

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 26661-13-2 4-N-benzoylcytosine 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 
• 107-46-0 Hexamethyldisiloxane 
• 10416-59-8 N,O-Bis(trimethylsilyl)acetamide 
• 98-88-4 benzoyl chloride 
• 4039-32-1 lithium hexamethyldisilazane 

Downstream Products

• 89622-54-8 N⁴-benzoylcytosine 1-methyl-2,3,4-tri-O-acetyl-β-D-glucopyranosiduronate 
• 162934-38-5 <4'-O-(p-Nitrobenzoyl)-2',3'-dideoxy-β-D-glycero-pent-2'-enopyranosyl>-N⁴-benzoylcytosine 
• 162934-39-6 <4'-O-(p-Nitrobenzoyl)-2',3'-dideoxy-α-D-glycero-pent-2'-enopyranosyl>-N⁴-benzoylcytosine 
• 195608-76-5 N-{1-[(3R,5S)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-methyl-isoxazolidin-5-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide 
• 210548-24-6 N-[1-((2S,4R,5S)-4-Benzyloxy-5-benzyloxymethyl-3,3-difluoro-tetrahydro-thiophen-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide 
• 210548-23-5 N-[1-((2R,4R,5S)-4-Benzyloxy-5-benzyloxymethyl-3,3-difluoro-tetrahydro-thiophen-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide 
• 210548-25-7 N⁴-benzoyl-1-(2-deoxy-3,5-dibenzoyl-2-C-methylene-4-thio-α-L-erythro-pentofuranosyl)cytosine 
• 210548-26-8 N⁴-benzoyl-1-(2-deoxy-3,5-dibenzoyl-2-C-methylene-4-thio-β-L-erythro-pentofuranosyl)cytosine 
• 301826-41-5 N⁴-benzoyl-1-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-β-D-glycero-tetrafuranosyl]cytosine 
• 301826-42-6 N⁴-benzoyl-1-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-α-D-glycero-tetrofuranosyl]cytosine 
• 273204-50-5 (2S,3R,4R,5R)-2-[4-(Benzoylamino)-2-oxo-1,2-dihydropyrimidin-1-yl]-5-[(2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}ethoxy)methyl]tetrahydrofuran-3,4-diyl diacetate 
• 177365-14-9 β-L-2',3'-dideoxy-3'-fluorocytidine 
• 177365-14-9 2',3'-dideoxy-3'-fluoro-α-L-cytidine 
• 405238-85-9 1-[5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-2-fluoro-β-D-glycero-pent-2-enofuranosyl]-N⁴-benzoylcytosine 

Relevant academic research and scientific papers

Synthesis and Anti-HCV Activities of 4′-Fluoro-2′-Substituted Uridine Triphosphates and Nucleotide Prodrugs: Discovery of 4′-Fluoro-2′- C-methyluridine 5′-Phosphoramidate Prodrug (AL-335) for the Treatment of Hepatitis C Infection

We report the synthesis and biological evaluation of a series of 4′-fluoro-2′-C-substituted uridines. Triphosphates of the uridine analogues exhibited a potent inhibition of hepatitis C virus (HCV) NS5B polymerase with IC50 values as low as 27 nM. In an HCV subgenomic replicon assay, the phosphoramidate prodrugs of these uridine analogues demonstrated a very potent activity with EC50 values as low as 20 nM. A lead compound AL-335 (53) demonstrated high levels of the nucleoside triphosphate in vitro in primary human hepatocytes and Huh-7 cells as well as in dog liver following a single oral dose. Compound 53 was selected for the clinical development where it showed promising results in phase 1 and 2 trials.

A general and enantioselective approach to pentoses: A rapid synthesis of PSI-6130, the nucleoside core of sofosbuvir

An efficient route towards biologically relevant pentose derivatives is described. The de novo synthetic strategy features an enantioselective α-oxidation reaction enabled by a chiral amine in conjunction with copper(II) catalysis. A subsequent Mukaiyama aldol coupling allows for the incorporation of a wide array of modular two-carbon fragments. Lactone intermediates accessed via this route provide a useful platform for elaboration, as demonstrated by the preparation of a variety of C-nucleosides and fluorinated pentoses. Finally, this work has facilitated expedient syntheses of pharmaceutically active compounds currently in clinical use.

Tetrofuranose nucleoside phosphonic acids: Synthesis and properties

New isoelectronic, non-isosteric phosphonate analogues of nucleoside 5'-phosphates featuring the phosphorus moiety directly attached on the sugar ring in the C4' position are described. The analogues were synthesised by a nucleosidation reaction from tetr

SEVEN-MEMBERED RING NUCLEOSIDES

The present invention provides nucleoside analogue Compounds that treat a host infected with a Flaviviridae virus infection, or other viruses that exhibit RNA- dependent RNA viral replication, compositions comprising" these Compounds and methods of using the Compounds for the treatment and/or Prophylaxis of viral infection, especially hepatitis C, in an infected host.

Ex-chiral-pool synthesis of β-hydroxyphosphonate nucleoside analogues

A new series of mononucleotide analogues bearing a nonhydrolysable P-C bond instead of the P-O phosphate linkage is presented. We intend to set up an approach that allows the synthesis of β-hydroxyphosphonate nucleoside analogues as a single diastereoisomer. In this respect, the key "sugar-phosphonate" intermediate was obtained through an Arbusov reaction from an iodosugar derivative in which the stereochemistry of the β-hydroxy group is determined by the choice of the starting material and remains in the resulting nucleotide analogues. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Synthesis of nucleoside analogues bearing the five naturally occurring nucleic acid bases built on a 2-oxabicylo[3.1.0]hexane scaffold

Hitherto unknown nucleoside analogues incorporating the five naturally occurring nucleic acid bases built on a 2-oxabicyclo[3.1.0]hexane template were synthesized. The synthesis of these new conformationally restricted nucleoside analogues involved the pr

A direct synthesis of nucleoside analogs homologated at the 3′- and 5′-positions

A new route is presented to prepare analogs of nucleosides homologated at the 3′- and 5′-positions. This route, applicable to both the D- and L-enantiomeric forms, is suitable for the preparation of monomeric bis-homonucleosides needed for the synthesis o

Stereoselective synthesis and antiviral activity of d-2′,3′-didehydro-2′,3′-dideoxy-2′-fluoro-4 ′-thionucleosides

As 2′,3′-didehydro-2′,3′-dideoxy-2′ -fluoronucleosides have exhibited interesting antiviral effects against HIV-1 as well as HBV, it is of interest to synthesize the isosterically substituted 4′-thionucleosides in which 4′-oxygen is replaced by a sulfur a

Structure-activity relationships of 2′-fluoro-2′,3′-unsaturated d-nucleosides as anti-hiv-1 agents

We studied the structure-activity relationships of a series of 2′-fluoro-2′,3′-unsaturated D-nucleosides against HIV-1 in human peripheral blood mononuclear (PBM) cells. The target compounds 10-21 and 28-33 were prepared by N-glycosylation of the acetate

Synthesis of 2',3'-dideoxy-3'-fluoro-L-ribonucleosides as potential antiviral agents from D-sorbitol

2',3'-Dideoxy-3'-fluoro-L-ribonucleosides were synthesized as potential antiviral agents. The key intermediate, methyl 5-O-benzoyl-2-3-dideoxy-3-fluoro-L-ribofuranoside, which was prepared from D-sorbitol, was condensed with pyrimidine and purine bases to obtain the respective nucleosides. Among them, the cytosine analogue 2',3'-dideoxy-3'-fluoro-α-L-cytidine showed a moderate anti-HBV activity. (C) 2000 Elsevier Science Ltd.