2'-Deoxy-2'-methyleneuridine

Base Information

• Chemical Name: 2'-Deoxy-2'-methyleneuridine
• CAS No.: 119410-95-6
• Molecular Formula: C10H12N2O5
• Molecular Weight: 240.216
• DSSTox Substance ID: DTXSID30454355
• Nikkaji Number: J371.756I
• Wikidata: Q82275838
• ChEMBL ID: CHEMBL2021334
• Mol file: 119410-95-6.mol

Synonyms:119410-95-6;2'-Deoxy-2'-methyleneuridine;1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methylideneoxolan-2-yl]pyrimidine-2,4-dione;SCHEMBL4295956;2'-deoxy-2'-methylene-uridine;2'-deoxy-2'-methylideneuridine;CHEMBL2021334;DTXSID30454355;MFCD00893186;Uridine, 2/'-deoxy-2/'-methylene-;CS-0164653;1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methylenetetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione? (sofosbuvir Impurity pound(c)

Chemical Property of 2'-Deoxy-2'-methyleneuridine

Chemical Property:

• Melting Point: 173.5 °C (decomp)
• PKA: 9.29±0.10(Predicted)
• PSA: 104.81000
• Density: 1.53±0.1 g/cm3(Predicted)
• LogP: -1.24430
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 240.07462149
• Heavy Atom Count: 17
• Complexity: 406

Purity/Quality:

97% ^*data from raw suppliers

2''-Deoxy-2''-methyleneuridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=C1C(C(OC1N2C=CC(=O)NC2=O)CO)O
• Isomeric SMILES: C=C1[C@@H]([C@H](O[C@H]1N2C=CC(=O)NC2=O)CO)O
• Uses: 2''-Deoxy-2''-methyleneuridine is an analog of Uridine (U829910) and has antiherpesvirus, antitumor, antiviral, and anticancer activity.

Technology Process of 2'-Deoxy-2'-methyleneuridine

There total 14 articles about 2'-Deoxy-2'-methyleneuridine 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: 100.0%

3',5'-di-O-acetyl-2'-deoxy-2'-methylene-β-D-uridine (146952-83-2) → 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methylenetetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (119410-95-6)

Guidance literature:

With triethylamine; In methanol; water; Ambient temperature;

DOI:10.1016/S0040-4039(00)60576-2

Reference yield: 99.0%

1-((6aR,8R,9aS)-2,2,4,4-tetraisopropyl-9-methylenetetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-pyrimidine-2,4(1H,3H)-dione (102789-14-0) → 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methylenetetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (119410-95-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2h;

DOI:10.1055/s-1991-26774

Reference yield: 99.0%

1-((2R,5R)-4-((tert-butyldimethylsilyl)oxy)-5-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)pyrimidine-2,4 (1H,3H)-dione (134660-24-5) → 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methylenetetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (119410-95-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2h;

DOI:10.1055/s-1991-26774

upstream raw materials:

1-((6aR,8R,9aS)-2,2,4,4-tetraisopropyl-9-methylenetetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-pyrimidine-2,4(1H,3H)-dione

1-((2R,5R)-4-((tert-butyldimethylsilyl)oxy)-5-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)pyrimidine-2,4 (1H,3H)-dione

3',5'-di-O-acetyl-2'-deoxy-2'-methylene-β-D-uridine

1-((6aR,8R,9aR)-2,2,4,4-tetraisopropyl-9-oxotetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)pyrimidine-2,4(1H,3H)-dione

Downstream raw materials:

2'-deoxy-2'-methylidene-5'-O-trityluridine

1-((2R,4S,5R)-5-Hydroxymethyl-3-methylene-4-trityloxy-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

(2R,3S,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-methylene-2-(((triisopropylsilyl)oxy)methyl)tetrahydrofuran-3-yl ((perfluorobenzoyl)oxy)carbamate

1-((2R,4S,5R)-4-hydroxy-3-methylene-5-(((triisopropylsilyl)oxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione