5,6-Dihydrouridine

Base Information

• Chemical Name: 5,6-Dihydrouridine
• CAS No.: 5627-05-4
• Molecular Formula: C9H14 N2 O6
• Molecular Weight: 246.22
• Hs Code.: 2934999090
• European Community (EC) Number: 822-987-4
• UNII: 0D5FR359JO
• DSSTox Substance ID: DTXSID6021329
• Nikkaji Number: J130.845I
• Wikipedia: Dihydrouridine
• Wikidata: Q413063
• Metabolomics Workbench ID: 37278
• ChEMBL ID: CHEMBL3237555
• Mol file: 5627-05-4.mol

Synonyms:3,4-dihydrouridine;5,6-dihydrouridine

Chemical Property of 5,6-Dihydrouridine

Chemical Property:

• Boiling Point: °Cat760mmHg
• PKA: 12.40±0.20(Predicted)
• Flash Point: °C
• PSA: 122.49000
• Density: 1.614g/cm³
• LogP: -2.57420
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 246.08518617
• Heavy Atom Count: 17
• Complexity: 335

Purity/Quality:

99% ^*data from raw suppliers

5,6-Dihydrouridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(C(=O)NC1=O)C2C(C(C(O2)CO)O)O
• Isomeric SMILES: C1CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
• General Description: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,3-diazinan-2-one, also known as dihydrouridine, is a ribonucleoside derivative that serves as a key intermediate in the study of RNA radical chemistry. It is generated photochemically and reacts under anaerobic conditions to form dihydrouridine (4), while aerobic conditions yield 6-hydroxy-5,6-dihydrouridine derivatives. 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,3-diazinan-2-one's reactivity, particularly as the 5,6-dihydrouridin-6-yl radical, makes it a valuable model for investigating oxidative RNA damage mechanisms.

Technology Process of 5,6-Dihydrouridine

There total 6 articles about 5,6-Dihydrouridine 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: 98.0%

uridine (58-96-8) → 5,6-dihydrouridine (5627-05-4)

Guidance literature:

With hydrogen; rhodium contaminated with carbon; In water; for 24h;

Reference yield: 78.0%

2',3'-O-(benzylidene)uridine (3257-71-4) → 5,6-dihydrouridine (5627-05-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 48h;

DOI:10.1021/ol048426w

Reference yield:

2′,3′-O-bis-(benzyloxycarbonyl)uridine (820212-19-9) → 5,6-dihydrouridine (5627-05-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / 1.4-cyclohexadiene / Pd/C / dimethylformamide / 1.5 h

2: 31 percent / POcl₃ / acetonitrile / 1 h / 0 °C

3: 78 percent / H₂ / Pd/C / ethanol / 48 h

With cyclohexa-1,4-diene; hydrogen; trichlorophosphate; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ol048426w

upstream raw materials:

uridine

2',3'-O-(benzylidene)uridine

2′,3′-O-bis-(benzyloxycarbonyl)uridine

5'-O-tert-butyldimethylsilyl-2',3'-O-bis(benzyloxycarbonyl)uridine

Downstream raw materials:

2',3',5'-trimesyloxy-5,6-dihydrouridine

5,6-Dihydro-5'-O-(4-methoxytrityl)uridin

Tetrahydrouridine

1-(β-D-ribofuranosyl)hexahydropyrimidin-2-one

Refernces

Photochemical generation and reactivity of the 5,6-dihydrouridin-6-yl radical

10.1021/jo9012805

The research aims to study the reactivity of RNA radicals, specifically the 5,6-dihydrouridin-6-yl radical, using photochemical methods. The study employs Norrish type I photocleavage of the tert-butyl ketone (2b) to generate the 5,6-dihydrouridin-6-yl radical (1b) and investigates its reactivity under aerobic and anaerobic conditions. Key chemicals used include ?-mercaptoethanol as a trapping agent, benzoyl groups for enhanced detection via HPLC, and various ribonucleoside derivatives as precursors and product standards. The study finds that the radical can be cleanly generated with high mass balances, and its reactivity is similar to but slightly less than that of its 2'-deoxyribonucleoside analogue. The major product formed in the presence of O2 is 5'-benzoyl-6-hydroxy-5,6-dihydrouridine (6), while under anaerobic conditions, dihydrouridine (4) is the primary product. The study concludes that the 5,6-dihydrouridin-6-yl radical is a useful model for studying RNA radical chemistry and its potential role in oxidative RNA damage.