85743-99-3

Basic information

• Product Name: Benzamide, N-[2-[(trimethylsilyl)oxy]-4-pyrimidinyl]-
• CAS NO: 85743-99-3
• Molecular Formula: C14H17N3O2Si
• Molecular Weight: 287.393
• Mol File: 85743-99-3.mol
• Article Data: 19

Chemical Properties

• CAS DataBase Reference: Benzamide, N-[2-[(trimethylsilyl)oxy]-4-pyrimidinyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzamide, N-[2-[(trimethylsilyl)oxy]-4-pyrimidinyl]-(85743-99-3)
• EPA Substance Registry System: Benzamide, N-[2-[(trimethylsilyl)oxy]-4-pyrimidinyl]-(85743-99-3)

Safety Data

• Hazardous Substances Data: 85743-99-3(Hazardous Substances Data)

Upstream product

• 26661-13-2 N₄-benzoylcitosine 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 26661-13-2 4-N-benzoylcytosine 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 
• 26661-13-2 N⁴-Benzoylcytosine 
• 10416-59-8 N,O-Bis(trimethylsilyl)acetamide 

Downstream Products

• 23624-64-8 N⁴-benzoyl-1-(2’,3’,5’-tri-O-benzoyl-β-D-ribofuranosyl)-cytosine 
• 335259-82-0 N-{1-[3-azido-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide 
• 335259-83-1 N-{1-[3-azido-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide 
• 479035-82-0 N⁴-benzoyl-1-(5-O-benzoyl-2,3-dideoxy-3,3-difluoro-β-D-ribofuranosyl)cytosine 
• 698391-73-0 N⁴-benzoyl-1-(5-O-benzoyl-2,3-dideoxy-3,3-difluoro-α-D-ribofuranosyl)cytosine 
• 1011761-53-7 C₂₂H₂₅N₃O₆ 
• 817204-32-3 (2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate 
• 1207737-70-9 C₂₇H₂₈N₄O₇ 
• 1219930-54-7 ethyl 2-((2R,3S,5S)-2-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-5-((tertbutyldiphenylsilyloxy)methyl)tetrahydrofuran-3-yl)-2-hydroxypropanoate 
• 874638-98-9 N-(1-((2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide 

Relevant articles and documents

Synthesis and biological evaluation of deuterated sofosbuvir analogs as HCV NS5B inhibitors with enhanced pharmacokinetic properties

A series of deuterated sofosbuvir analogs were designed and prepared with the aim of improving their pharmacokinetic properties. The devised synthetic routes allow for site-selective deuterium incorporation with high levels of isotopic purity. As expected, the deuterated analogs (37-44) are as efficacious as sofosbuvir when tested in vitro inhibition of viral replication (replicon) assays. Compared with sofosbuvir, deuterated analog 40 displays improved in vivo pharmacokinetics profiles in rats and dogs in terms of the metabolite and the prodrug. The Cmax and area under the curve (AUC) of 40 in dogs were increased by 3.4- and 2.7-fold, respectively. Due to the enhanced pharmacokinetic properties and the great synthetic advantage of an inexpensive deuterium source (D2O) for 40, it was chosen for further investigation.

Stereoselective Synthesis of Sofosbuvir through Nucleoside Phosphorylation Controlled by Kinetic Resolution

The preparation of Sofosbuvir, the potent key component of recent Hepatitis C (HCV) infection therapies, is reported. The process is based on the dynamic kinetic resolution of the stereochemically unstable isopropyl-2-{[chloro(phenoxy)phosphoryl]-amino}propanoate (8). A high stereoselectivity was obtained when the right protective group for 3′-OH was chosen. Ester and carbonate-based protective groups gave lower stereoselectivities, but benzyl protection allowed the phosphorylation to occur with a 92:8 ratio in favour of the product with the right configuration at the P-stereogenic centre. Starting from the γ-lactone of 2-deoxy-2-fluoro-2-methylpentonic acid, the synthesis was accomplished in eight steps in 40 % overall yield using commercially available reagents, and without any enzymatic or chemical resolution technique.

Intermediate compound for synthesis of sofosbuvir and synthetic method thereof

The invention discloses an intermediate compound for synthesis of sofosbuvir and a synthetic method thereof; the intermediate compound comprises 4 intermediate products and 1 target compound, wherein the 4 intermediate products include methyl ((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-5-hydroxy-4-methyltetrahydrofuran-2-yl) benzoate, methyl ((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-5-chloro-4-methyltetrahydrofuran-2-yl) benzoate, (2'R)-N-benzoyl-2'-deoxy-2'-fluoro-2'-methylcytidine 3',5'-dibenzoate, and ((2R,3R,4R,5R)-3-(benzoyloxy)-4-fluoro-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-methyltetrahydrofuran-2-yl) methyl benzoic acid, and the target compound is (2'R)-2'-deoxy-2'-fluoro-2'-methylcytidine. Compared with existing synthetic methods, the synthetic method has high content of target compound and has little impurities generated in the synthetic process; the results of the synthetic method are stable, the synthetic method is simple to perform and is applicable to large-scale industrial production and technical popularization.