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
• Uses: 5,6-Dihydrouridine is an intermediate used in the synthesis of 3,4,5,6-Tetrahydrouridine (>80%) (T310250), which is a derivative of Uridine (U829910). Tetrahydrouridine (THU) is a potent inhibitor of cytidine. It inhibits cell proliferation through cell cycle regulation regardless of cytidine deaminase expression levels deaminase (CDA), and thus can be used as a potential and promising treatment for tumors with highly expressed CDA.

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:

Tetrahydrouridine

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

2',3'-O-isopropylidene-5,6-dihydrouridine

2',3'-Bis-O-(tert-butyldiphenylsilyl)-5,6-dihydro-5'-O-(4-methoxytrityl)uridin

Refernces

• 1、 Fourrey,J.-L.,Jouin,P.. "-". . p. 3397 - 3400. Retrieved 1977.
• 2、 Price, Neil P.J.,Jackson, Michael A.,Vermillion, Karl E.,Blackburn, Judith A.,Li, Jiakun,Yu, Biao. "Selective catalytic hydrogenation of the N-acyl and uridyl double bonds in the tunicamycin family of protein N-glycosylation inhibitors". . p. 1122 - 1128. Retrieved 2017.
• 3、 Luvino, Delphine,Smietana, Michael,Vasseur, Jean-Jacques. "Selective fluorescence-based detection of dihydrouridine with boronic acids". . p. 9253 - 9256. Retrieved 2008/02/10.