1-((2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxyMethyl)-3-Methyltetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione

Base Information

• Chemical Name: 1-((2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxyMethyl)-3-Methyltetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione
• CAS No.: 114262-49-6
• Molecular Formula: C10H14N2O6
• Molecular Weight: 258.231
• Mol file: 114262-49-6.mol

Synonyms:1-((2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxyMethyl)-3-Methyltetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione;Sofosbuvir Impurity 12;Sofosbuvir metabolites GS331007

Chemical Property of 1-((2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxyMethyl)-3-Methyltetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione

Chemical Property:

• Melting Point: 132-135 °C
• PKA: 9.39±0.10(Predicted)
• PSA: 124.78000
• Density: 1.572±0.06 g/cm3(Predicted)
• LogP: -2.46180

Purity/Quality:

≥95% ^*data from raw suppliers

1-β-D-Arabinofuranosyluracil-2-C-methyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 1-β-D-Arabinofuranosyluracil-2-C-methyl is an impurity of PSI-7977 (P839640), a prodrug that is metabolized to the active antiviral agent 2''-deoxy-2''-α-fluoro-β-C-methyluridine-5''-monophosphate and is currently being investigated in phase 3 clinical trials for the treatment of hepatitis C. Studies have profiled PSI-7977 as a nucleotide inhibitor of hepatitis C virus, exerting selective inhibitory effects towards HCV NS5B polymerase.

Technology Process of 1-((2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxyMethyl)-3-Methyltetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione

There total 1 articles about 1-((2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxyMethyl)-3-Methyltetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(2R,3R,4S,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-hydroxy-4-methyl-2-((2,2,2-trifluoroacetoxy)methyl)tetrahydrofuran-3-yl 2,2,2-trifluoroacetate → 2'-deoxy-2'-fluoro-2'-methyluridine (863329-66-2,2041584-99-8) + 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methylenetetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (119410-95-6) + 1-(2'-C-methyl-β-D-arabinofuranosyl)uracil (114262-49-6)

Guidance literature:

(2R,3R,4S,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-hydroxy-4-methyl-2-((2,2,2-trifluoroacetoxy)methyl)tetrahydrofuran-3-yl 2,2,2-trifluoroacetate; With triethylamine tris(hydrogen fluoride); triethylamine; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate; In dichloromethane; at 20 ℃; for 4h; Inert atmosphere;

With water;

Reference yield: 86.0%

(S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester (1334513-02-8,1627824-09-2) + 1-(2'-C-methyl-β-D-arabinofuranosyl)uracil (114262-49-6) → (S)-isopropyl 2-(((S)-(((2R,3R,4S,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-di-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino) propanoate (2095551-10-1)

Guidance literature:

With pyridine; dimethylaluminum chloride; In hexane; at 0 - 50 ℃; for 25h; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.7b00469

Reference yield: 59.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + 1-(2'-C-methyl-β-D-arabinofuranosyl)uracil (114262-49-6) → 1-(5'-O-(4,4'-dimethoxytrityl)-2'-C-methyl-β-D-arabinofuranosyl)uracil

Guidance literature:

With pyridine; for 27h; Ambient temperature;

DOI:10.1016/0040-4020(95)00452-E

Downstream raw materials:

((2R,3R,4S,5R)-3-(benzoyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-hydroxy-4-methyltetrahydrofuran-2-yl)methyl benzoate

2'-deoxy-2'-fluoro-2'-methyluridine

1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methylenetetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

(2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate

Refernces